Citation: Guoping Yang, Xuanjie Xie, Mengyuan Cheng, Xiaofei Gao, Xiaoling Lin, Ke Li, Yuanyuan Cheng, Yufeng Liu. H₄SiW₁₂O₄₀-catalyzed cyclization of epoxides/aldehydes and sulfonyl hydrazides: An efficient synthesis of 3, 4-disubstituted 1H-pyrazoles[J]. Chinese Chemical Letters, ;2022, 33(3): 1483-1487. doi: 10.1016/j.cclet.2021.08.037 shu

H₄SiW₁₂O₄₀-catalyzed cyclization of epoxides/aldehydes and sulfonyl hydrazides: An efficient synthesis of 3, 4-disubstituted 1H-pyrazoles

Guoping Yang ^{a, *,} ,
Xuanjie Xie ^a ,
Mengyuan Cheng ^b ,
Xiaofei Gao ^a ,
Xiaoling Lin ^a ,
Ke Li ^a ,
Yuanyuan Cheng ^{a, *,} ,
Yufeng Liu ^{a, *,}

a.
Jiangxi Key Laboratory for Mass Spectrometry and Instrumentation, Jiangxi Province Key Laboratory of Synthetic Chemistry, East China University of Technology, Nanchang 330013, China
b.
Henan Key Laboratory of Polyoxometalate Chemistry, College of Chemistry and Chemical Engineering, Henan University, Kaifeng 475004, China

erick@ecut.edu.cn

201860095@ecut.edu.cn

yfliu@ecut.edu.cn

Received Date: 24 June 2021
Revised Date: 6 August 2021
Accepted Date: 8 August 2021
Available Online: 12 August 2021

Figures(6)

A simple and efficient method for the synthesis of pyrazoles through a silicotungstic acid (H₄SiW₁₂O₄₀)-catalyzed cyclization of epoxides/aldehydes and sulfonyl hydrazides has been developed. Various epoxides/aldehydes were smoothly reacted with sulfonyl hydrazides to furnish regioselectivity 3, 4-disubstituted 1H-pyrazoles. The application of such an earth-abundant, readily accessible, and nontoxic catalyst provides a green approach for the construction of 3, 4-disubstituted 1H-pyrazoles. A plausible reaction mechanism has been proposed on the basis of control experiments, GC-MS and DFT calculations.
- Silicotungstic acid,
- Epoxides,
- Aldehydes,
- Sulfonyl hydrazides,
- 3, 4-Disubstituted 1H-pyrazoles
In recent decades, the Daphniphyllum alkaloids have drawn a lot of interest from our community due to their intriguing biological activity and fascinating cage-like structures [1-9]. The groups of Heathcock [10-13], Carreira [14], Li [15-19], Smith [20,21], Hanessian [22], Fukuyama/Yokoshima [23], Dixon [24,25], Zhai [26,27], Qiu [28,29], Gao [30], Sarpong [31,32], Li [33], Lu [34] and Li [35] successively reported their impressive synthesis of more than thirty Daphniphyllum alkaloids. Also, our group accomplished the total synthesis of ten Daphniphyllum alkaloids from six different subfamilies, including himalensine A, 10-deoxydaphnipaxianine A, daphlongamine E and calyciphylline R (calyciphylline A-type), dapholdhamine B (daphnezomine A-type), caldaphnidine O (bukittinggine-type), caldaphnidine J (yuzurimine-type), daphnezomine L methyl ester and calyciphylline K (daphnezomine L-type) and caldaphnidine D (secodaphniphylline-type) [36-41].

Since Hirata's seminal discovery in 1966, nearly fifty yuzurimine-type (or macrodaphniphyllamine-type) alkaloids—or about one-sixth of all Daphniphyllum alkaloids now known—have been identified (Fig. 1). It is acknowledged that the individuals within this subfamily possess intricate and caged hexacyclic skeleton, thus presents significant synthetic challenge. In 2020, our group achieved the first total synthesis of a member within this subfamily, caldaphnidine J [39]. Later, Li reported their impressive total synthesis of five macrodaphniphyllamine-type alkaloids [19].

Figure 1

Figure 1. Representative yuzurimine-type alkaloids.

DownLoad: Full-Size Img PowerPoint

Based on the biosynthetic pathway of yuzurimine-type alkaloids [6,8], it is reasonable to assume that C₁₄–epi-deoxycalyciphylline H could be an actual member of the yuzurimine-type alkaloid subfamily, yet to be isolated. As our interests in natural product synthesis continues [42-44], we wish to describe here our endeavor towards the total synthesis of calyciphylline H [45] that led us to finally access one of its close derivatives, C₁₄–epi-deoxycalyciphylline H.

As depicted in Scheme 1, the retrosynthetic analysis of calyciphylline H indicated that it could be derived from C₁₄–epi-deoxycalyciphylline H via C-14 epimerization and a Polonovski reaction [19]. Next, we envisioned that an enyne cycloisomerization of compound 1 would allow facile access to the key tetrahydropyrrole motif as well as the C3-C4 alkene motif in our target molecules. Next, it was envisaged that compound 1 could be synthesized from compound 2 via homologation and propargylation. One of the critical five-membered rings in compound 2 could be fabricated via a Prins reaction from aldehyde 3. This aldehyde compound was envisioned to be derived from the tetracyclic compound 4, which can be produced from tricycle 5 through our previously reported procedures [37-39].

Scheme 1

Scheme 1. Retrosynthetic analysis.

DownLoad: Full-Size Img PowerPoint

Our study commenced from known tricyclic compound 5, which was converted to vicinal diol 4 via a 7-step procedure involving ring-expansion and cyclopentane formation (Scheme 2) [37-39]. Then, under Ando's olefination conditions (p-TSA, CH(OMe)₃; then Ac₂O, 150 ℃) [46], alkene 6 was effectively derivatized from diol 4 in excellent yield (93%). Removal of the benzyl group in compound 6 suffered partial N-detosylation under sodium naphthalene conditions, hence, re-tosylation was necessary to provide a satisfactory yield of compound 7. A facile Dess-Martin oxidation of the primary hydroxyl group in compound 7 furnished aldehyde 3 in nearly quantitative yield. Next, under the acidic conditions (TfOH, 0 ℃), a Prins reaction was triggered between the aldehyde motif and the alkene motif in compound 3, fabricating alcohols 2a (56%) and 2b (38%). The absolute stereochemical configuration of 2a was unambiguously assigned via a single-crystal X-Ray diffraction (CCDC: 2258010), while that of 2b was assigned by its conversion to 2a via oxidation and reduction. At this point, a homologation was required for introducing the C-14 carboxylic acid ester moiety. To this end, a Dess-Martin oxidation of the mixture of 2a and 2b yielded the corresponding ketone compound, which unfortunately failed to react under various homologation conditions (Wittig, Peterson, MeLi, MeMgBr, Nysted, Van Leusen). Gratifyingly, treating it with Horner-Wadsworth-Emmons conditions (8, n-BuLi) [37-39,41] successfully gave homologated product 9. Following hydrolysis of the ketene dithioacetal moiety in compound 9 yielded compound 10 with an α-faced carboxylic acid ester at C-14. This outcome was attributed to its thermodynamically favored stereochemistry, which was assigned by a single-crystal XRD (CCDC: 2258012). Replacement of the N-tosyl group with the propargyl group afforded enyne compound 1 in 92% yield. Finally, a Pd-catalyzed enyne cycloisomerization [47] produced key tetrahydropyrrole motif as well as the C3-C4 alkene motif in the corresponding diene, which was further selectively hydrogenated (H₂, Crabtree's catalyst) to yield C₁₄–epi-deoxycalyciphylline H. In addition, transformation of this compound to natural calyciphylline H is currently under investigation.

Scheme 2

Scheme 2. Total synthesis of C₁₄–epi-deoxycalyciphylline H, a putative yuzurimine-type alkaloid and synthetic study towards the daphnezomine L-type alkaloid paxdaphnidine A.

DownLoad: Full-Size Img PowerPoint

Next, our attention turned to a complex member of daphnezomine L-type alkaloids, paxdaphnidine A. It was envisioned that a S_N2-substitution reaction using a cyanide anion may set the desired stereogenic configuration at C-14. Bearing this in mind, alcohol 2a was converted to its epimer, 2b, which was then sulfonylated to give compound 11. Heating this compound with NBu₄CN in DMF produced nitrile 12 with the desired stereogenic outcome, which was also unambiguously confirmed by a single-crystal XRD (CCDC: 2258013). It should be noted that other attempts of this type of transformation gave lower yields (-OMs, NaCN, DMSO, 120 ℃, 41%; -OEs, NaCN, DMF or DMSO, 130 ℃, < 10%; -OTs, NaCN, DMF, 130 ℃, 43%; -OTs, NaCN, DMSO, 130 ℃, 26%). More experimental evidence further indicated the thermodynamical bias at C-14. When subjecting nitrile 12 to DIBAL-H (−78 ℃ to 0 ℃) followed by a Pinnick oxidation (0 ℃ to room temperature) and methylation, compound 10 with the undesired C-14 stereogenic center was produced as the main product. However, when the DIBAL-H reduction as well as the Pinnick oxidation was carefully performed at −78 ℃, compound 13 was successfully produced with the desired C-14 stereochemistry. Afterwards, detosylation and propargylation of compound 13 produced tertiary amine 14. Next, a Pd-catalyzed enyne cycloisomerization forged the tetrahydropyrrole ring. The so-afforded hexacyclic diene was then subjected to the von Braun reaction conditions (BrCN, K₂CO₃) [41,48,49] to cleave the C—N bond in a regioselective manner to give compound 15. This regioselectivity was likely dominated by the drastically different steric hindrances between three C—N bonds. The final-stage transformation of compound 15 to paxdaphnidine A, is still under investigation in our laboratory.

In summary, the total synthesis of C₁₄–epi-deoxycalyciphylline H, a possible yuzurimine-type alkaloid family member and a close derivative of its natural congener calyciphylline H, was accomplished. Key cyclization methods, such as Prins reaction and enyne cycloisomerization paved the road to the target molecule. Synthesis towards a daphnezomine L-type alkaloid, paxdaphnidine A, was also studied, featuring a late-stage von Braun reaction. Our findings may benefit the research in this active field—Daphniphyllum alkaloid synthesis.

Declaration of competing interest

The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.

Acknowledgments

Financial support from the National Natural Science Foundation of China (Nos. 21971104 and 22271136), Shenzhen Key Laboratory of Small Molecule Drug Discovery and Synthesis (No. ZDSYS20190902093215877), Guangdong Provincial Key Laboratory of Catalysis (No. 2020B121201002), Guangdong Innovative Program (No. 2019BT02Y335), Education Department of Guangdong Province, Key research projects in colleges and universities in Guangdong Province (No. 2021ZDZX2035), Shenzhen Nobel Prize Scientists Laboratory Project (No. C17783101) and Innovative Team of Universities in Guangdong Province (No. 2020KCXTD016) is greatly appreciated. We also thank SUSTech CRF NMR facility and Dr. Yang Yu (SUSTech) for HRMS analysis. We also thank Dr. X. Chang (SUSTech) for single crystal X-ray diffraction analysis.

Supplementary materials

Supplementary material associated with this article can be found, in the online version, at doi:10.1016/j.cclet.2023.108733.

References
1. [1]
  A. Ansari, A. Ali, M. Asif, et al., New J. Chem. 41(2017) 16-41. doi: 10.1039/C6NJ03181A
2. [2]
  J.V. Faria, P.F. Vegi, A.G.C. Miguita, et al., Biorg. Med. Chem. 25(2017) 5891-5903. doi: 10.1016/j.bmc.2017.09.035
3. [3]
  D. Havrylyuk, B. Zimenkovsky, O. Vasylenko, et al., J. Med. Chem. 55(2012) 8630-8641. doi: 10.1021/jm300789g
4. [4]
  Ş. G. Küçükgüzel, S. Şenkardeş, Eur. J. Med. Chem. 97(2015) 786-815. doi: 10.1016/j.ejmech.2014.11.059
5. [5]
  V. Kumar, K. Kaur, G.K. Gupta, et al., Eur. J. Med. Chem. 69(2013) 735-753. doi: 10.1016/j.ejmech.2013.08.053
6. [6]
  X.H. Lv, Z.L. Ren, D.D. Li, et al., Chin. Chem. Lett. 28(2017) 377-382. doi: 10.1016/j.cclet.2016.10.029
7. [7]
  L. Catala, K. Wurst, D.B. Amabilino, et al., J. Mater. Chem. 16(2006) 2736-2745. doi: 10.1039/b604598g
8. [8]
  I.L. Dalinger, A.V. Kormanov, K.Y. Suponitsky, et al., Chem. Asian J. 13(2018) 1165-1172. doi: 10.1002/asia.201800214
9. [9]
  A.L. Rheingold, L.N. Zakharov, S. Trofimenko, Inorg. Chem. 42(2003) 827-833. doi: 10.1021/ic0205280
10. [10]
  U.P. Singh, S. Kashyap, H.J. Singh, et al., CrystEngComm 13(2011) 4110-4120. doi: 10.1039/c0ce00820f
11. [11]
  P. Yin, C. He, J.N.M. Shreeve, J. Mater. Chem. A 4(2016) 1514-1519. doi: 10.1039/C5TA09999D
12. [12]
  S. Fustero, M. Sánchez-Roselló, P. Barrio, et al., Chem. Rev. 111(2011) 6984-7034. doi: 10.1021/cr2000459
13. [13]
  Y.L. Janin, Chem. Rev. 112(2012) 3924-3958. doi: 10.1021/cr200427q
14. [14]
  M. Li, B.X. Zhao, Eur. J. Med. Chem. 85(2014) 311-340. doi: 10.1016/j.ejmech.2014.07.102
15. [15]
  P. Zhao, Z. Zeng, X. Feng, et al., Chin. Chem. Lett. 32(2021) 132-135. doi: 10.1016/j.cclet.2020.11.053
16. [16]
  L. Hao, H. Liu, Z. Zhang, et al., Chin. Chem. Lett. 32(2021) 2309-2312. doi: 10.1016/j.cclet.2021.02.025
17. [17]
  M. Zora, A. Kivrak, C. Yazici, J. Org. Chem. 76(2011) 6726-6742. doi: 10.1021/jo201119e
18. [18]
  B.H. Zhang, L.S. Lei, S.Z. Liu, et al., Chem. Commun. 53(2017) 8545-8548. doi: 10.1039/C7CC04610C
19. [19]
  Q. Wang, L. He, K.K. Li, et al., Org. Lett. 19(2017) 658-661. doi: 10.1021/acs.orglett.6b03822
20. [20]
  G. Ji, X. Wang, S. Zhang, et al., Chem. Commun. 50(2014) 4361-4363. doi: 10.1039/C4CC01280A
21. [21]
  X. Deng, N.S. Mani, Org. Lett. 10(2008) 1307-1310. doi: 10.1021/ol800200j
22. [22]
  J. Sun, J.K. Qiu, Y.L. Zhu, et al., J. Org. Chem. 80(2015) 8217-8224. doi: 10.1021/acs.joc.5b01280
23. [23]
  S. Zhao, K. Chen, L. Zhang, et al., Adv. Synth. Catal. 362(2020) 3516-3541. doi: 10.1002/adsc.202000466
24. [24]
  C. Zhu, H. Zeng, C. Liu, et al., Org. Lett. 22(2020) 809-813. doi: 10.1021/acs.orglett.9b04228
25. [25]
  Y.Q. Jiang, J. Li, Z.W. Feng, et al., Adv. Synth. Catal. 362(2020) 2609-2614. doi: 10.1002/adsc.202000233
26. [26]
  Z. Wang, W.M. He, Chin. J. Org. Chem. 39(2019) 3594-3595. doi: 10.6023/cjoc201900002
27. [27]
  J. Zhang, Y. Shao, H. Wang, et al., Org. Lett. 16(2014) 3312-3315. doi: 10.1021/ol501312s
28. [28]
  G.P. Yang, S.X. Shang, B. Yu, et al., Inorg. Chem. Front. 5(2018) 2472-2477. doi: 10.1039/C8QI00678D
29. [29]
  G.P. Yang, X. He, B. Yu, et al., Appl. Organomet. Chem. 32(2018) e4532. doi: 10.1002/aoc.4532
30. [30]
  T. Zhang, Y. Meng, J. Lu, et al., Adv. Synth. Catal. 360(2018) 3063-3068. doi: 10.1002/adsc.201701200
31. [31]
  H. Zhang, Q. Wei, G. Zhu, et al., Tetrahedron Lett. 57(2016) 2633-2637. doi: 10.1016/j.tetlet.2016.05.020
32. [32]
  J. Wen, Y. Fu, R.Y. Zhang, et al., Tetrahedron 67(2011) 9618-9621. doi: 10.1016/j.tet.2011.09.074
33. [33]
  L. Tang, M. Ma, Q. Zhang, et al., Adv. Synth. Catal. 359(2017) 2610-2620. doi: 10.1002/adsc.201700196
34. [34]
  Y. Guo, G. Wang, L. Wei, et al., J. Org. Chem. 84(2019) 2984-2990. doi: 10.1021/acs.joc.8b02897
35. [35]
  M. Yoshimatsu, K. Ohta, N. Takahashi, Chem. Eur J. 18(2012) 15602-15606. doi: 10.1002/chem.201202828
36. [36]
  S.X. Xu, L. Hao, T. Wang, et al., Org. Biomol. Chem. 11(2013) 294-298. doi: 10.1039/C2OB27016A
37. [37]
  L. Wu, M. Shi, J. Org. Chem. 75(2010) 2296-2301. doi: 10.1021/jo100105k
38. [38]
  W.M. Shu, K.L. Zheng, J.R. Ma, et al., Org. Lett. 17(2015) 1914-1917. doi: 10.1021/acs.orglett.5b00605
39. [39]
  M.C. Pérez-Aguilar, C. Valdés, Angew. Chem. Int. Ed. 52(2013) 7219-7223. doi: 10.1002/anie.201301284
40. [40]
  G.P. Yang, Y.F. Liu, K. Li, et al., Chin. Chem. Lett. 31(2020) 3233-3236. doi: 10.1016/j.cclet.2020.07.018
41. [41]
  G.P. Yang, Y.F. Liu, X.L. Lin, et al., Chin. Chem. Lett. 33(2022) 354-357. doi: 10.1016/j.cclet.2021.05.008
42. [42]
  G.P. Yang, X. Wu, B. Yu, et al., ACS Sustain. Chem. Eng. 7(2019) 3727-3732. doi: 10.1021/acssuschemeng.8b06445
43. [43]
  M.T. Lv, Y.F. Liu, K. Li, et al., Tetrahedron Lett. 65(2021) 152757. doi: 10.1016/j.tetlet.2020.152757
44. [44]
  M. Smith, R. Hunter, N. Stellenboom, et al., Biochim. Biophys. Acta Gen. Subj. 1860(2016) 1439-1449. doi: 10.1016/j.bbagen.2016.03.032
45. [45]
  Z. Lian, B.N. Bhawal, P. Yu, et al., Science 356(2017) 1059-1063. doi: 10.1126/science.aam9041
46. [46]
  Y. Shi, S. Li, Y. Lu, et al., Chem. Commun. 56(2020) 2131-2134. doi: 10.1039/C9CC09262E
47. [47]
  J. Meinwald, S.S. Labana, M.S. Chadha, J. Am. Chem. Soc. 85(1963) 582-585. doi: 10.1021/ja00888a022
1. [1]
  A. Ansari, A. Ali, M. Asif, et al., New J. Chem. 41(2017) 16-41. doi: 10.1039/C6NJ03181A
2. [2]
  J.V. Faria, P.F. Vegi, A.G.C. Miguita, et al., Biorg. Med. Chem. 25(2017) 5891-5903. doi: 10.1016/j.bmc.2017.09.035
3. [3]
  D. Havrylyuk, B. Zimenkovsky, O. Vasylenko, et al., J. Med. Chem. 55(2012) 8630-8641. doi: 10.1021/jm300789g
4. [4]
  Ş. G. Küçükgüzel, S. Şenkardeş, Eur. J. Med. Chem. 97(2015) 786-815. doi: 10.1016/j.ejmech.2014.11.059
5. [5]
  V. Kumar, K. Kaur, G.K. Gupta, et al., Eur. J. Med. Chem. 69(2013) 735-753. doi: 10.1016/j.ejmech.2013.08.053
6. [6]
  X.H. Lv, Z.L. Ren, D.D. Li, et al., Chin. Chem. Lett. 28(2017) 377-382. doi: 10.1016/j.cclet.2016.10.029
7. [7]
  L. Catala, K. Wurst, D.B. Amabilino, et al., J. Mater. Chem. 16(2006) 2736-2745. doi: 10.1039/b604598g
8. [8]
  I.L. Dalinger, A.V. Kormanov, K.Y. Suponitsky, et al., Chem. Asian J. 13(2018) 1165-1172. doi: 10.1002/asia.201800214
9. [9]
  A.L. Rheingold, L.N. Zakharov, S. Trofimenko, Inorg. Chem. 42(2003) 827-833. doi: 10.1021/ic0205280
10. [10]
  U.P. Singh, S. Kashyap, H.J. Singh, et al., CrystEngComm 13(2011) 4110-4120. doi: 10.1039/c0ce00820f
11. [11]
  P. Yin, C. He, J.N.M. Shreeve, J. Mater. Chem. A 4(2016) 1514-1519. doi: 10.1039/C5TA09999D
12. [12]
  S. Fustero, M. Sánchez-Roselló, P. Barrio, et al., Chem. Rev. 111(2011) 6984-7034. doi: 10.1021/cr2000459
13. [13]
  Y.L. Janin, Chem. Rev. 112(2012) 3924-3958. doi: 10.1021/cr200427q
14. [14]
  M. Li, B.X. Zhao, Eur. J. Med. Chem. 85(2014) 311-340. doi: 10.1016/j.ejmech.2014.07.102
15. [15]
  P. Zhao, Z. Zeng, X. Feng, et al., Chin. Chem. Lett. 32(2021) 132-135. doi: 10.1016/j.cclet.2020.11.053
16. [16]
  L. Hao, H. Liu, Z. Zhang, et al., Chin. Chem. Lett. 32(2021) 2309-2312. doi: 10.1016/j.cclet.2021.02.025
17. [17]
  M. Zora, A. Kivrak, C. Yazici, J. Org. Chem. 76(2011) 6726-6742. doi: 10.1021/jo201119e
18. [18]
  B.H. Zhang, L.S. Lei, S.Z. Liu, et al., Chem. Commun. 53(2017) 8545-8548. doi: 10.1039/C7CC04610C
19. [19]
  Q. Wang, L. He, K.K. Li, et al., Org. Lett. 19(2017) 658-661. doi: 10.1021/acs.orglett.6b03822
20. [20]
  G. Ji, X. Wang, S. Zhang, et al., Chem. Commun. 50(2014) 4361-4363. doi: 10.1039/C4CC01280A
21. [21]
  X. Deng, N.S. Mani, Org. Lett. 10(2008) 1307-1310. doi: 10.1021/ol800200j
22. [22]
  J. Sun, J.K. Qiu, Y.L. Zhu, et al., J. Org. Chem. 80(2015) 8217-8224. doi: 10.1021/acs.joc.5b01280
23. [23]
  S. Zhao, K. Chen, L. Zhang, et al., Adv. Synth. Catal. 362(2020) 3516-3541. doi: 10.1002/adsc.202000466
24. [24]
  C. Zhu, H. Zeng, C. Liu, et al., Org. Lett. 22(2020) 809-813. doi: 10.1021/acs.orglett.9b04228
25. [25]
  Y.Q. Jiang, J. Li, Z.W. Feng, et al., Adv. Synth. Catal. 362(2020) 2609-2614. doi: 10.1002/adsc.202000233
26. [26]
  Z. Wang, W.M. He, Chin. J. Org. Chem. 39(2019) 3594-3595. doi: 10.6023/cjoc201900002
27. [27]
  J. Zhang, Y. Shao, H. Wang, et al., Org. Lett. 16(2014) 3312-3315. doi: 10.1021/ol501312s
28. [28]
  G.P. Yang, S.X. Shang, B. Yu, et al., Inorg. Chem. Front. 5(2018) 2472-2477. doi: 10.1039/C8QI00678D
29. [29]
  G.P. Yang, X. He, B. Yu, et al., Appl. Organomet. Chem. 32(2018) e4532. doi: 10.1002/aoc.4532
30. [30]
  T. Zhang, Y. Meng, J. Lu, et al., Adv. Synth. Catal. 360(2018) 3063-3068. doi: 10.1002/adsc.201701200
31. [31]
  H. Zhang, Q. Wei, G. Zhu, et al., Tetrahedron Lett. 57(2016) 2633-2637. doi: 10.1016/j.tetlet.2016.05.020
32. [32]
  J. Wen, Y. Fu, R.Y. Zhang, et al., Tetrahedron 67(2011) 9618-9621. doi: 10.1016/j.tet.2011.09.074
33. [33]
  L. Tang, M. Ma, Q. Zhang, et al., Adv. Synth. Catal. 359(2017) 2610-2620. doi: 10.1002/adsc.201700196
34. [34]
  Y. Guo, G. Wang, L. Wei, et al., J. Org. Chem. 84(2019) 2984-2990. doi: 10.1021/acs.joc.8b02897
35. [35]
  M. Yoshimatsu, K. Ohta, N. Takahashi, Chem. Eur J. 18(2012) 15602-15606. doi: 10.1002/chem.201202828
36. [36]
  S.X. Xu, L. Hao, T. Wang, et al., Org. Biomol. Chem. 11(2013) 294-298. doi: 10.1039/C2OB27016A
37. [37]
  L. Wu, M. Shi, J. Org. Chem. 75(2010) 2296-2301. doi: 10.1021/jo100105k
38. [38]
  W.M. Shu, K.L. Zheng, J.R. Ma, et al., Org. Lett. 17(2015) 1914-1917. doi: 10.1021/acs.orglett.5b00605
39. [39]
  M.C. Pérez-Aguilar, C. Valdés, Angew. Chem. Int. Ed. 52(2013) 7219-7223. doi: 10.1002/anie.201301284
40. [40]
  G.P. Yang, Y.F. Liu, K. Li, et al., Chin. Chem. Lett. 31(2020) 3233-3236. doi: 10.1016/j.cclet.2020.07.018
41. [41]
  G.P. Yang, Y.F. Liu, X.L. Lin, et al., Chin. Chem. Lett. 33(2022) 354-357. doi: 10.1016/j.cclet.2021.05.008
42. [42]
  G.P. Yang, X. Wu, B. Yu, et al., ACS Sustain. Chem. Eng. 7(2019) 3727-3732. doi: 10.1021/acssuschemeng.8b06445
43. [43]
  M.T. Lv, Y.F. Liu, K. Li, et al., Tetrahedron Lett. 65(2021) 152757. doi: 10.1016/j.tetlet.2020.152757
44. [44]
  M. Smith, R. Hunter, N. Stellenboom, et al., Biochim. Biophys. Acta Gen. Subj. 1860(2016) 1439-1449. doi: 10.1016/j.bbagen.2016.03.032
45. [45]
  Z. Lian, B.N. Bhawal, P. Yu, et al., Science 356(2017) 1059-1063. doi: 10.1126/science.aam9041
46. [46]
  Y. Shi, S. Li, Y. Lu, et al., Chem. Commun. 56(2020) 2131-2134. doi: 10.1039/C9CC09262E
47. [47]
  J. Meinwald, S.S. Labana, M.S. Chadha, J. Am. Chem. Soc. 85(1963) 582-585. doi: 10.1021/ja00888a022
1. [1]
  Tian-Yu Gao , Xiao-Yan Mo , Shu-Rong Zhang , Yuan-Xu Jiang , Shu-Ping Luo , Jian-Heng Ye , Da-Gang Yu . Visible-light photoredox-catalyzed carboxylation of aryl epoxides with CO₂. Chinese Chemical Letters, 2024, 35(7): 109364-. doi: 10.1016/j.cclet.2023.109364
2. [2]
  Hong-Tao Ji , Yu-Han Lu , Yan-Ting Liu , Yu-Lin Huang , Jiang-Feng Tian , Feng Liu , Yan-Yan Zeng , Hai-Yan Yang , Yong-Hong Zhang , Wei-Min He . Nd@C₃N₄-photoredox/chlorine dual catalyzed synthesis and evaluation of antitumor activities of 4-alkylated sulfonyl ketimines. Chinese Chemical Letters, 2025, 36(2): 110568-. doi: 10.1016/j.cclet.2024.110568
3. [3]
  Lei Shen , Yang Zhang , Linlin Zhang , Chuanwang Liu , Zhixian Ma , Kangjiang Liang , Chengfeng Xia . Phenylhydrazone anions excitation for the photochemical carbonylation of aryl iodides with aldehydes. Chinese Chemical Letters, 2024, 35(4): 108742-. doi: 10.1016/j.cclet.2023.108742
4. [4]
  Kun Tang , Fen Su , Shijie Pan , Fengfei Lu , Zhongfu Luo , Fengrui Che , Xingxing Wu , Yonggui Robin Chi . Enones from aldehydes and alkenes by carbene-catalyzed dehydrogenative couplings. Chinese Chemical Letters, 2024, 35(9): 109495-. doi: 10.1016/j.cclet.2024.109495
5. [5]
  Zhikang Wu , Guoyong Dai , Qi Li , Zheyu Wei , Shi Ru , Jianda Li , Hongli Jia , Dejin Zang , Mirjana Čolović , Yongge Wei . POV-based molecular catalysts for highly efficient esterification of alcohols with aldehydes as acylating agents. Chinese Chemical Letters, 2024, 35(8): 109061-. doi: 10.1016/j.cclet.2023.109061
6. [6]
  Yi-Fan Wang , Hao-Yun Yu , Hao Xu , Ya-Jie Wang , Xiaodi Yang , Yu-Hui Wang , Ping Tian , Guo-Qiang Lin . Rhodium(Ⅲ)-catalyzed diastereo- and enantioselective hydrosilylation/cyclization reaction of cyclohexadienone-tethered α, β-unsaturated aldehydes. Chinese Chemical Letters, 2024, 35(9): 109520-. doi: 10.1016/j.cclet.2024.109520
7. [7]
  Jinyuan Cui , Tingting Yang , Teng Xu , Jin Lin , Kunlong Liu , Pengxin Liu . Hydrogen spillover enhances the selective hydrogenation of α,β-unsaturated aldehydes on the Cu-O-Ce interface. Chinese Journal of Structural Chemistry, 2025, 44(1): 100438-100438. doi: 10.1016/j.cjsc.2024.100438
8. [8]
  Runze Liu , Yankai Bian , Weili Dai . Qualitative and quantitative analysis of Brønsted and Lewis acid sites in zeolites: A combined probe-assisted 1H MAS NMR and NH3-TPD investigation. Chinese Journal of Structural Chemistry, 2024, 43(4): 100250-100250. doi: 10.1016/j.cjsc.2024.100250
9. [9]
  Hua Liu , Jian Zhao , Qi Li , Xiang-Yu Zhang , Zhi-Wei Zheng , Kun Huang , Da-Bin Qin , Bin Zhao . Indium-captured zirconium-porphyrin frameworks displaying rare multi-selectivity for catalytic transfer hydrogenation of aldehydes and ketones. Chinese Chemical Letters, 2025, 36(6): 110593-. doi: 10.1016/j.cclet.2024.110593
10. [10]
  Yanfen PENG , Xinyue WANG , Tianbao LIU , Xiaoshuo WU , Yujing WEI . Syntheses and luminescence of four Cd(Ⅱ)/Zn(Ⅱ) complexes constructed by 1,3‐bis(4H‐1,2,4‐triazole)benzene. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1416-1426. doi: 10.11862/CJIC.20250018
11. [11]
  Xun Zhu , Chenchen Zhang , Yingying Li , Yin Lu , Na Huang , Dawei Wang . Degradation of perfluorooctanoic acid by inductively heated Fenton-like process over the Fe₃O₄/MIL-101 composite. Chinese Chemical Letters, 2024, 35(12): 109753-. doi: 10.1016/j.cclet.2024.109753
12. [12]
  Cailing Wu , Shaojie Wu , Qifei Huang , Kai Sun , Xianqiang Huang , Jianji Wang , Bing Yu . Potassium-modified carbon nitride photocatalyzed-aminoacylation of N-sulfonyl ketimines. Chinese Chemical Letters, 2025, 36(2): 110250-. doi: 10.1016/j.cclet.2024.110250
13. [13]
  Zhen Liu , Zhi-Yuan Ren , Chen Yang , Xiangyi Shao , Li Chen , Xin Li . Asymmetric alkenylation reaction of benzoxazinones with diarylethylenes catalyzed by B(C₆F₅)₃/chiral phosphoric acid. Chinese Chemical Letters, 2024, 35(5): 108939-. doi: 10.1016/j.cclet.2023.108939
14. [14]
  Jing LIANG , Qian WANG , Junfeng BAI . Synthesis and structures of cdq-topological quaternary and (4, 4, 8)-c topological quinary Zn-MOFs with both oxalic acid and triazole ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2186-2192. doi: 10.11862/CJIC.20240177
15. [15]
  Weizhong LING , Xiangyun CHEN , Wenjing LIU , Yingkai HUANG , Yu LI . Syntheses, crystal structures, and catalytic properties of three zinc(Ⅱ), cobalt(Ⅱ) and nickel(Ⅱ) coordination polymers constructed from 5-(4-carboxyphenoxy)nicotinic acid. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1803-1810. doi: 10.11862/CJIC.20240068
16. [16]
  Junying LI , Xinyan CHEN , Xihui DIAO , Muhammad Yaseen , Chao CHEN , Hao WANG , Chuansong QI , Wei LI . Chiral fluorescent sensor Tb³⁺@Cd-CP based on camphoric acid for the enantioselective recognition of R- and S-propylene glycol. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2497-2504. doi: 10.11862/CJIC.20240084
17. [17]
  Yuexiang Liu , Xiangqiao Yang , Tong Lin , Guantian Yang , Xiaoyong Xu , Bubing Zeng , Zhong Li , Weiping Zhu , Xuhong Qian . Efficient continuous synthesis of 2-[3-(trifluoromethyl)phenyl]malonic acid, a key intermediate of Triflumezopyrim, coupling with esterification-condensation-hydrolysis. Chinese Chemical Letters, 2025, 36(1): 109747-. doi: 10.1016/j.cclet.2024.109747
18. [18]
  Haitao Yin , Liang Meng , Li Li , Jiamu Xiao , Longrui Liang , Nannan Huang , Yansong Shi , Angang Zhao , Jingwen Hou . Polydopamine-modified biochar supported polylactic acid and zero-valent iron affects the functional microbial community structure for 1,1,1-trichloroethane removal in simulated groundwater. Chinese Chemical Letters, 2025, 36(1): 110313-. doi: 10.1016/j.cclet.2024.110313
19. [19]
  Ao Sun , Zipeng Li , Shuchun Li , Xiangbao Meng , Zhongtang Li , Zhongjun Li . Stereoselective synthesis of α-3-deoxy-D-manno-oct-2-ulosonic acid (α-Kdo) derivatives using a C3-p-tolylthio-substituted Kdo fluoride donor. Chinese Chemical Letters, 2025, 36(3): 109972-. doi: 10.1016/j.cclet.2024.109972
20. [20]
  Gaofeng WANG , Shuwen SUN , Yanfei ZHAO , Lixin MENG , Bohui WEI . Structural diversity and luminescence properties of three zinc coordination polymers based on bis(4-(1H-imidazol-1-yl)phenyl)methanone. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 849-856. doi: 10.11862/CJIC.20230479