Cp*Co(Ⅲ)-catalyzed C-H amidation of azines with dioxazolones
-
* Corresponding authors.
E-mail addresses: pichao@zzu.edu.cn (C. Pi), cuixl@zzu.edu.cn (X. Cui).
Citation:
Yanzhen Huang, Chao Pi, Zhen Tang, Yangjie Wu, Xiuling Cui. Cp*Co(Ⅲ)-catalyzed C-H amidation of azines with dioxazolones[J]. Chinese Chemical Letters,
;2020, 31(12): 3237-3240.
doi:
10.1016/j.cclet.2020.08.046
T. Naito, Chem. Pharm. Bull. 56(2008) 1367-1383.
doi: 10.1248/cpb.56.1367
Y. Wu, B. Tian, C. Hu, et al., Org. Biomol. Chem. 17(2019) 5505-5508.
doi: 10.1039/C9OB00740G
C. Sambiagio, S.P. Marsden, A.J. Blacker, P.C. McGowan, Chem. Soc. Rev. 43(2014) 3525-3550.
doi: 10.1039/C3CS60289C
S. Bhunia, G.G. Pawar, S.V. Kumar, Y. Jiang, D. Ma, Angew. Chem. Int. Ed. 56(2017) 16136-16179.
doi: 10.1002/anie.201701690
C. Torborg, M. Beller, Adv. Synth. Catal. 351(2009) 3027-3043.
doi: 10.1002/adsc.200900587
F. Monnier, M. Taillefer, Angew. Chem. Int. Ed. 48(2009) 6954-6971.
doi: 10.1002/anie.200804497
Y. Park, Y. Kim, S. Chang, Chem. Rev. 117(2017) 9247-9301.
doi: 10.1021/acs.chemrev.6b00644
Y. Park, K.T. Park, J.G. Kim, S. Chang, J. Am. Chem. Soc. 137(2015) 4534-4542.
doi: 10.1021/jacs.5b01324
Y. Park, S. Jee, J.G. Kim, S. Chang, Org. Process Res. Dev. 19(2015) 1024-1029.
doi: 10.1021/acs.oprd.5b00164
J.A. Souto, P. Becker, Á. Iglesias, K. Muñiz, J. Am. Chem. Soc. 134(2012) 15505-15511.
doi: 10.1021/ja306211q
C. You, T. Yuan, Y. Huang, et al., Org. Biomol. Chem. 16(2018) 4728-4733.
doi: 10.1039/C8OB01108G
K. Shin, H. Kim, S. Chang, Acc. Chem. Res. 48(2015) 1040-1052.
doi: 10.1021/acs.accounts.5b00020
C. Pi, X. Cui, Y. Wu, J. Org. Chem. 80(2015) 7333-7339.
doi: 10.1021/acs.joc.5b01377
J.Y. Kim, S.H. Park, J. Ryu, et al., J. Am. Chem. Soc. 134(2012) 9110-9113.
doi: 10.1021/ja303527m
S.H. Park, J. Kwak, K. Shin, et al., J. Am. Chem. Soc. 136(2014) 2492-2502.
doi: 10.1021/ja411072a
L. Jie, L. Wang, D. Xiong, et al., J. Org. Chem. 83(2018) 10974-10984.
doi: 10.1021/acs.joc.8b01618
Y. Feng, Y. Li, Y. Yu, L. Wang, X. Cui, RSC Adv. 8(2018) 8450-8454.
doi: 10.1039/C8RA00524A
L. Xu, L. Wang, Y. Feng, et al., Org. Lett. 19(2017) 4343-4346.
doi: 10.1021/acs.orglett.7b02028
Y. Li, Y. Feng, L. Xu, L. Wang, X. Cui, Org. Lett. 18(2016) 4924-4927.
doi: 10.1021/acs.orglett.6b02406
B. Zhu, X. Cui, C. Pi, D. Chen, Y. Wu, Adv. Synth. Catal. 358(2016) 326-332.
doi: 10.1002/adsc.201501036
Y. Feng, Z. Zhang, Q. Fu, et al., Chin. Chem. Lett. 31(2020) 58-60.
doi: 10.1016/j.cclet.2019.05.013
H. Jung, H. Keum, J. Kweon, S. Chang, J. Am. Chem. Soc. 142(2020) 5811-5818.
doi: 10.1021/jacs.0c00868
D. Dev, N.B. Palakurthy, K. Thalluri, J. Chandra, B. Mandal, J. Org. Chem. 79(2014) 5420-5431.
doi: 10.1021/jo500292m
J. Senger, J. Melesina, M. Marek, et al., J. Med. Chem. 59(2016) 1545-1555.
doi: 10.1021/acs.jmedchem.5b01493
S. Huang, H. Li, X. Sun, L. Xu, L. Wang, X. Cui, Org. Lett. 21(2019) 5570-5574.
doi: 10.1021/acs.orglett.9b01902
L. Xu, T. Li, L. Wang, X. Cui, J. Org. Chem. 84(2019) 560-567.
doi: 10.1021/acs.joc.8b02396
X.H. Hu, X.F. Yang, T.P. Loh, ACS Catal. 6(2016) 5930-5934.
doi: 10.1021/acscatal.6b02015
J. Park, S. Chang, Angew. Chem. Int. Ed. 54(2015) 14103-14107.
doi: 10.1002/anie.201505820
Y. Park, K.T. Park, J.G. Kim, S. Chang, J. Am. Chem. Soc. 137(2015) 4534-4542.
doi: 10.1021/jacs.5b01324
X. Mi, W. Feng, C. Pi, X. Cui, J. Org. Chem. 84(2019) 5305-5312.
doi: 10.1021/acs.joc.9b00300
Y. He, C. Pi, Y. Wu, X. Cui, Chin. Chem. Lett. 31(2020) 396-400.
doi: 10.1016/j.cclet.2019.09.025
J. Ren, C. Pi, Y. Wu, X. Cui, Org. Lett. 21(2019) 4067-4071.
doi: 10.1021/acs.orglett.9b01246
N.K. Mishra, Y. Oh, M. Jeon, et al., Eur. J. Org. Chem. 2016(2016) 4976-4980.
doi: 10.1002/ejoc.201601096
K.M. van Vliet, B. de Bruin, ACS Catal. 10(2020) 4751-4769.
doi: 10.1021/acscatal.0c00961
G. Le Goff, J. Ouazzani, Bioorg. Med. Chem. 22(2014) 6529-6544.
doi: 10.1016/j.bmc.2014.10.011
L.M. Blair, J. Sperry, J. Nat. Prod. 76(2013) 794-812.
doi: 10.1021/np400124n
Y. Zhu, H. Jin, Y. Huang, Chem. Commun. (Camb.) 55(2019) 10135-10137.
doi: 10.1039/C9CC05276C
W. Tang, Y. Xiang, A. Tong, J. Org. Chem. 74(2009) 2163-2166.
doi: 10.1021/jo802631m
C. Chakravarty, B. Mandal, P. Sarkar, J. Phys. Chem. C 122(2018) 3245-3255.
doi: 10.1021/acs.jpcc.7b11609
M.X. Wu, Y.W. Yang, Chin. Chem. Lett. 28(2017) 1135-1143.
doi: 10.1016/j.cclet.2017.03.026
W. Han, G. Zhang, G. Li, H. Huang, Org. Lett. 16(2014) 3532-3535.
doi: 10.1021/ol501483k
J. Wen, A. Wu, M. Wang, J. Zhu, J. Org, Chem. 80(2015) 10457-10463.
J. Wen, A. Wu, Y. Miao, J. Zhu, Tetrahedron Lett. 56(2015) 5512-5516.
doi: 10.1016/j.tetlet.2015.08.025
Y. Yu, C. Kuai, R. Chauvin, et al., J. Org. Chem. 82(2017) 8611-8616.
doi: 10.1021/acs.joc.7b01472
D.S. Deshmukh, P.A. Yadav, B.M. Bhanage, Org. Biomol. Chem.17(2019) 3489-3496.
doi: 10.1039/C9OB00174C
H.M. Vu, J.Y. Yong, F.W. Chen, X.Q. Li, G.Q. Shi, J. Org. Chem. 85(2020) 4963-4972.
doi: 10.1021/acs.joc.0c00138
P.W. Tan, A.M. Mak, M.B. Sullivan, D.J. Dixon, J. Seayad, Angew. Chem. Int. Ed. 56(2017) 16550-16554.
doi: 10.1002/anie.201709273
J.S. Sun, M. Liu, J. Zhang, L. Dong, J. Org. Chem. 83(2018) 10555-10563.
doi: 10.1021/acs.joc.8b01354
J. Park, S. Chang, Angew. Chem. Int. Ed. 54(2015) 14103-14107.
doi: 10.1002/anie.201505820
Y. Liu, F. Xie, A.Q. Jia, X. Li, Chem. Commun. (Camb.) 54(2018) 4345-4348.
doi: 10.1039/C8CC01447G
B. Khan, V. Dwivedi, B. Sundararaju, Adv. Synth. Catal. 362(2020) 1195-1200.
doi: 10.1002/adsc.201901267
J. Huang, J. Ding, T.M. Ding, et al., Org. Lett. 21(2019) 7342-7345.
doi: 10.1021/acs.orglett.9b02632
D.-G. Yu, M. Suri, F. Glorius, J. Am. Chem. Soc. 135(2013) 8802-8805.
doi: 10.1021/ja4033555
C. Brouwer, K. Jenko, S.S. Zoghbi, R.B. Innis, V.W. Pike, J. Med. Chem. 57(2014) 6240-6251.
doi: 10.1021/jm5007947
C.P. Jones, K.W. Anderson, S.L. Buchwald, J. Org. Chem. 72(2007) 7968-7973.
doi: 10.1021/jo701384n
J. Huang, Y. Chen, A.O. King, et al., Org. Lett. 10(2008) 2609-2612.
doi: 10.1021/ol800837z
C. Eidamshaus, T. Triemer, H.U. Reissig, Synthesis 2011(2011) 3261-3266.
doi: 10.1055/s-0030-1260198
A. Fuerstner, A. Hupperts, A. Ptock, E. Janssen, J. Org. Chem. 59(1994) 5215-5229.
doi: 10.1021/jo00097a024
A. Fuerstner, A. Hupperts, J. Am. Chem. Soc. 117(1995) 4468-4475.
doi: 10.1021/ja00121a004
A. Fürstner, D.N. Jumbam, Tetrahedron 48(1992) 5991-6010.
doi: 10.1016/S0040-4020(01)89848-3
Y. Liang, Y.F. Liang, C. Tang, Y. Yuan, N. Jiao, Chem. Eur. J. 21(2015) 16395-16399.
doi: 10.1002/chem.201503533
P. Shi, L. Wang, K. Chen, J. Wang, J. Zhu, Org. Lett. 19(2017) 2418-2421.
doi: 10.1021/acs.orglett.7b00968
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
Yang Li , Yanan Dong , Zhihong Wei , Changzeng Yan , Zhen Li , Lin He , Yuehui Li . Fluoride-promoted Ni-catalyzed cyanation of C–O bond using CO2 and NH3. Chinese Chemical Letters, 2025, 36(5): 110206-. doi: 10.1016/j.cclet.2024.110206
Ting WANG , Peipei ZHANG , Shuqin LIU , Ruihong WANG , Jianjun ZHANG . A Bi-CP-based solid-state thin-film sensor: Preparation and luminescence sensing for bioamine vapors. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1615-1621. doi: 10.11862/CJIC.20240134
Ying Zhao , Yin-Hang Chai , Tian Chen , Jie Zheng , Ting-Ting Li , Francisco Aznarez , Li-Long Dang , Lu-Fang Ma . Size-controlled synthesis and near-infrared photothermal response of Cp* Rh-based metalla[2]catenanes and rectangular metallamacrocycles. Chinese Chemical Letters, 2024, 35(6): 109298-. doi: 10.1016/j.cclet.2023.109298
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
Zhenkang Ai , Hui Chen , Xuebin Liao . Nickel-catalyzed decarboxylative difluoromethylation and alkylation of alkenes. Chinese Chemical Letters, 2025, 36(3): 109954-. doi: 10.1016/j.cclet.2024.109954
Kongchuan Wu , Dandan Lu , Jianbin Lin , Ting-Bin Wen , Wei Hao , Kai Tan , Hui-Jun Zhang . Elucidating ligand effects in rhodium(Ⅲ)-catalyzed arene–alkene coupling reactions. Chinese Chemical Letters, 2024, 35(5): 108906-. doi: 10.1016/j.cclet.2023.108906
Long Jin , Jian Han , Dongmei Fang , Min Wang , Jian Liao . Pd-catalyzed asymmetric carbonyl alkynylation: Synthesis of axial chiral ynones. Chinese Chemical Letters, 2024, 35(6): 109212-. doi: 10.1016/j.cclet.2023.109212
Chen Li , Ziyuan Zhao , Shouyun Yu . Photoredox-catalyzed C-glycosylation of peptides with glycosyl bromides. Chinese Chemical Letters, 2024, 35(6): 109128-. doi: 10.1016/j.cclet.2023.109128
Ying-Di Hao , Zhi-Qian Lin , Xiao-Yu Guo , Jiao Liang , Can-Kun Luo , Qian-Tao Wang , Li Guo , Yong Wu . Rhodium-catalyzed Doyle-Kirmse rearrangement reactions of sulfoxoniun ylides. Chinese Chemical Letters, 2024, 35(4): 108834-. doi: 10.1016/j.cclet.2023.108834
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
Xiao-Bo Liu , Ren-Ming Liu , Xiao-Di Bao , Hua-Jian Xu , Qi Zhang , Yu-Feng Liang . Nickel-catalyzed reductive formylation of aryl halides via formyl radical. Chinese Chemical Letters, 2024, 35(12): 109783-. doi: 10.1016/j.cclet.2024.109783
Minjun Yin , Yuhui Lin , Manli Zhuang , Wei Xiao , Jie Wu . Photoredox-catalyzed synthesis of α,α-difluoromethyl-β-alkoxysulfones from sulfur dioxide. Chinese Chemical Letters, 2025, 36(3): 109926-. doi: 10.1016/j.cclet.2024.109926
Minghui Zhang , Na Zhang , Qian Zhao , Chao Wang , Alexander Steiner , Jianliang Xiao , Weijun Tang . Cobalt pincer complex-catalyzed highly enantioselective hydrogenation of quinoxalines. Chinese Chemical Letters, 2025, 36(4): 110081-. doi: 10.1016/j.cclet.2024.110081
Yanxin Jiang , Kwai Wun Cheng , Zhiping Yang , Jun (Joelle) Wang . Pd-catalyzed enantioselective and regioselective asymmetric hydrophosphorylation and hydrophosphinylation of enynes. Chinese Chemical Letters, 2025, 36(5): 110231-. doi: 10.1016/j.cclet.2024.110231
Wujun Jian , Mong-Feng Chiou , Yajun Li , Hongli Bao , Song Yang . Cu-catalyzed regioselective diborylation of 1,3-enynes for the efficient synthesis of 1,4-diborylated allenes. Chinese Chemical Letters, 2024, 35(5): 108980-. doi: 10.1016/j.cclet.2023.108980
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
Yiqian Jiang , Zihan Yang , Xiuru Bi , Nan Yao , Peiqing Zhao , Xu Meng . Mediated electron transfer process in α-MnO2 catalyzed Fenton-like reaction for oxytetracycline degradation. Chinese Chemical Letters, 2024, 35(8): 109331-. doi: 10.1016/j.cclet.2023.109331
Jing-Qi Tao , Shuai Liu , Tian-Yu Zhang , Hong Xin , Xu Yang , Xin-Hua Duan , Li-Na Guo . Photoinduced copper-catalyzed alkoxyl radical-triggered ring-expansion/aminocarbonylation cascade. Chinese Chemical Letters, 2024, 35(6): 109263-. doi: 10.1016/j.cclet.2023.109263
Yue Sun , Liming Yang , Yaohang Cheng , Guanghui An , Guangming Li . Pd(I)-catalyzed ring-opening arylation of cyclopropyl-α-aminoamides: Access to α-ketoamide peptidomimetics. Chinese Chemical Letters, 2024, 35(6): 109250-. doi: 10.1016/j.cclet.2023.109250