Synthesis of phosphanaphthalenes and nido-carborane fused six-membered phosphacycles
-
* Corresponding author.
E-mail address: duanzheng@zzu.edu.cn (Z. Duan).
Citation:
Guanyu Tao, Feichao Yang, Lujun Zhang, Yang Li, Zheng Duan, François Mathey. Synthesis of phosphanaphthalenes and nido-carborane fused six-membered phosphacycles[J]. Chinese Chemical Letters,
;2021, 32(1): 194-197.
doi:
10.1016/j.cclet.2020.11.018
P.L. Floch, Coord. Chem. Rev. 250(2006) 627-681.
doi: 10.1016/j.ccr.2005.04.032
(a) A. Fukazawa, Y. Sato, T. Higashiyama, et al., Chem. Commun. (Camb.) 52(2016) 1120-1123;
(b) C. Müller, D. Wasserberg, D. Vogt, et al., Chem. Eur. J. 13(2007) 4548-4559;
(c) N. Hashimoto, R. Umano, O. Yusuke, et al., J. Am. Chem. Soc. 140(2018) 2046-2049;
(d) A. Belyaev, Y. Chen, Z. Liu, et al., Chem. Eur. J. 25(2019) 6332-6341;
(e) W. Ye, X. Li, H. Tian, et al., J. Org. Chem. 85(2020) 3879-3886;
(f) P. Hindenberg, C. Romero-Nieto, Synlett 27(2016) 2293-2300.
(a) E.D. Matveeva, D.S. Vinogradov, N.S. Zefirov, et al., Eur. J. Org. Chem. 2015(2015) 7324-7333;
(b) E.D. Matveeva, T.A. Podrugina, N.S. Zefirov, et al., J. Org. Chem. 78(2013) 11691-11697;
(c) E.D. Matveeva, T.A. Podrugina, N.S. Zefirov, et al., Tetrahedron 69(2013) 7395-7402;
(d) E.D. Matveeva, T.A. Podrugina, N.S. Zefirov, et al., J. Org. Chem. 77(2012) 5770-5774;
(e) E.D. Matveeva, T.A. Podrugina, N.S. Zefirov, et al., J. Org. Chem. 74(2009) 9428-9432;
(f) A. Savateev, Y. Vlasenko, N. Shtil, A. Kostyuk, Eur. J. Inorg. Chem. 2016(2016) 628-632.
(a) A. Belyaev, Y. Chen, S. Su, I.O. Koshevoy, et al., Chem. Commun. (Camb. ) 53(2017) 10954-10957;
(b) P. Hindenberg, M. Busch, A. Paul, C. Romero-Nieto, et al., Angew. Chem. Int. Ed. 57(2018) 15157-15161;
(c) T. Kato, T. Kuwabara, Y. Minami, T. Hiyama, Y. Ishii, Bull. Chem. Soc. Jpn. 92(2019) 1131-1141;
(d) T. Delouche, A. Vacher, E. Caytan, P.A. Bouit, et al., Chem. Eur. J. 26(2020) 8226-8229.
(a) Y.V. Svyaschenko, B.B. Barnych, D.M. Volochnyuk, N.V. Shevchuk, A.N. Kostyuk, J. Org. Chem. 76(2011) 6125-6133;
(b) Y.V. Svyaschenko, A.N. Kostyuk, B.B. Barnych, D.M. Volochnyuk, Tetrahedron 63(2007) 5656-5664;
(c) A.N. Kostyuk, Y.V. Svyaschenko, D.M. Volochnyuk, Tetrahedron 61(2005) 9263-6272.
K. Dimroth, Delocalized posphorus-carbon double bonds, Heidelberg, Phosphorus-Carbon Double Bonds Fortschritte der Chemischen Forschung, 38/1, Springer, Berlin, 1973, doi: http://dx.doi.org/10.1007/BFb0051365.
G. Pfeifer, F. Chahdoura, M. Papke, et al., Chem. Eur. J. 26(2020) 10534-10543.
doi: 10.1002/chem.202000932
(a) L. Zhang, W. Yu, C. Liu, et al., Organometallics 34(2015) 5697-5702;
(b) L. Zhang, F. Yang, G. Tao, et al., Eur. J. Inorg. Chem. 17(2017) 2355-2362;
(c) H. Huang, Z. Wei, J. Hou, et al., Eur. J. Org. Chem. 22(2018) 2863-2869;
(d) J. Hou, Y. Xu, Z. Gan, et al., J. Organomet. Chem. 879(2019) 158-161;
(e) D. Wu, C. Hu, L. Qiu, Z. Duan, F. Mathey, Eur. J. Org. Chem. 37(2019) 6369-6376;
(f) E. Si, P. Zhao, L. Wang, Z. Duan, F. Mathey, Eur. J. Org. Chem. 6(2020) 697-701.
X.F. Zhu, C.E. Henry, O. Kwon, J. Am. Chem. Soc. 129(2007) 6722-6723.
doi: 10.1021/ja071990s
A. Bhunia, T. Roy, R.G. Gonnade, A.T. Biju, Org. Lett. 16(2014) 5132-5135.
doi: 10.1021/ol502490t
(a) A.R. Popescu, F. Teixidor, C. Viñas, Coord. Chem. Rev. 269(2014) 54-84;
(b) M. Joost, L. Estévez, K. Miqueu, A. Amgoune, D. Bourissou, Angew. Chem. Int. Ed. 127(2015) 5325-5329;
(c) Y.O. Wong, M.D. Smith, D.V. Peryshkov, Chem. Eur. J. 22(2016) 6764-6767;
(d) J.A. Ioppolo, J.K. Clegg, L.M. Rendina, Dalton Trans. 20(2007) 1982-1985;
(e) C.X. Cui, S. Ren, Z. Qiu, Z. Xie, Dalton Trans. 47(2018) 2453-2459;
(f) L.E. Riley, A.J. Welch, Claire L. McMullin, et al., Dalton Trans. 46(2017) 5218-5228;
(g) P. Coburger, E. Hey-Hawkins, et al., Inorg. Chem. 56(2017) 292-304.
(a) A. Kreienbrink, M.B. Sárosi, E.G. Rys, P. Lönnecke, E. Hey-Hawkins, Angew. Chem. Int. Ed. 50(2011) 4701-4703;
(b) A. Kreienbrink, M.B. Sárosi, R. Kuhnert, et al., Chem. Commun. (Camb. ) 51(2015) 836-838;
(c) J. Schulz, A. Kreienbrink, P. Coburger, et al., Chem. Eur. J. 24(2018) 6208-6216;
(d) G. Tao, Z. Duan, F. Mathey, Org. Lett. 21(2019) 2273-2276.
Yao Zou , Difei Gong , Haiguang Yang , Hongmei Yu , Guorong He , Ningbo Gong , Lianhua Fang , Guanhua Du , Yang Lu . Prediction, screening, characterization, antioxidant and antihypoxic effects of multi-component zwitterionic cocrystals of dietary flavonoids with picolinic acid. Chinese Chemical Letters, 2025, 36(9): 110768-. doi: 10.1016/j.cclet.2024.110768
Congzhao Dong , Yajun Zhang , Yingpu Bi , Zeyu Li , Yong Ding . Band structure engineering of phosphorus doped Ta3N5 for efficient photoelectrochemical water oxidation. Chinese Chemical Letters, 2025, 36(12): 111449-. doi: 10.1016/j.cclet.2025.111449
Sirui Chen , Ran Zhao , Li Dong , Qilin Liu , Wei Chen , Danna Liu , Maosheng Ye , Yingbo Li , Qiong Nie , Jingxin Meng , Shutao Wang . Smart antifouling coating integrating zwitterionic hydrogel with pH-responsive microcapsules for anti-crystal biofilm of orthodontic appliances. Chinese Chemical Letters, 2025, 36(12): 111647-. doi: 10.1016/j.cclet.2025.111647
Zhiwei Chen , Heyun Sheng , Xue Li , Menghan Chen , Xin Li , Qiuling Song . Efficient capture of difluorocarbene by pyridinium 1,4-zwitterionic thiolates: A concise synthesis of difluoromethylene-containing 1,4-thiazine derivatives. Chinese Chemical Letters, 2024, 35(4): 108937-. doi: 10.1016/j.cclet.2023.108937
Yizhe Chen , Yuzhou Jiao , Liangyu Sun , Cheng Yuan , Qian Shen , Peng Li , Shiming Zhang , Jiujun Zhang . Nonmetallic phosphorus alloying to regulate the oxygen reduction mechanisms of platinum catalyst. Chinese Chemical Letters, 2025, 36(4): 110789-. doi: 10.1016/j.cclet.2024.110789
Abiduweili Sikandaier , Yukun Zhu , Dongjiang Yang . In-situ decorated cobalt phosphide cocatalyst on Hittorf's phosphorus triggering efficient photocatalytic hydrogen production. Chinese Journal of Structural Chemistry, 2024, 43(2): 100242-100242. doi: 10.1016/j.cjsc.2024.100242
Jie Zhou , Chuanxiang Zhang , Changchun Hu , Shuo Li , Yuan Liu , Zhu Chen , Song Li , Hui Chen , Rokayya Sami , Yan Deng . Electrochemical aptasensor based on black phosphorus-porous graphene nanocomposites for high-performance detection of Hg2+. Chinese Chemical Letters, 2024, 35(11): 109561-. doi: 10.1016/j.cclet.2024.109561
Xiuxiu Jia , Tao Yin , Nianpeng Li , Hua Zhang , Anxian Shi , Abdukader Abdukayum , Sanshuang Gao , Guangzhi Hu . Reticulated lanthanum (La) carbonate-carbon composite for efficient phosphorus removal from eutrophic wastewater. Chinese Chemical Letters, 2025, 36(6): 110398-. doi: 10.1016/j.cclet.2024.110398
Luyun Zhang , Ding Liu , Huri Piao , Zhenhua Jia , Fen-Er Chen . A modified Bis-OPNN phosphorus ligand for Rh-catalyzed linear-selective hydroformylation of alkenes. Chinese Chemical Letters, 2025, 36(7): 110640-. doi: 10.1016/j.cclet.2024.110640
Long Huang , Jian Pu , Yunyu Zhao , Xiangxiang Fang , Yingjian Yu , Yuan Li , Jinyan Ma , Yuejin Zhu , Fang Hu , Chuang Yue . Phosphorus-doped carbon as an effective protective layer for advanced aqueous zinc-ion batteries. Chinese Chemical Letters, 2025, 36(8): 110989-. doi: 10.1016/j.cclet.2025.110989
Bingbing Dong , Junmin Zhang , Xiang-Yu Ye , Xuan Huang , Yonggui Robin Chi . Catalytic construction of P-stereogenic center via phosphorus-centered nucleophilic substitution. Chinese Chemical Letters, 2025, 36(9): 111052-. doi: 10.1016/j.cclet.2025.111052
Bo Yang , Suqiong Yan , Shirong Ban , Wei Huang . New horizons in phosphorus-based emitters: From circularly polarized fluorescence to room-temperature phosphorescence. Chinese Chemical Letters, 2025, 36(11): 110837-. doi: 10.1016/j.cclet.2025.110837
Mei-Chen Liu , Qing-Song Liu , Yi-Zhou Quan , Jia-Ling Yu , Gang Wu , Xiu-Li Wang , Yu-Zhong Wang . Phosphorus-silicon-integrated electrolyte additive boosts cycling performance and safety of high-voltage lithium-ion batteries. Chinese Chemical Letters, 2024, 35(8): 109123-. doi: 10.1016/j.cclet.2023.109123
Yuhao Ma , Yufei Zhou , Mingchuan Yu , Cheng Fang , Shaoxia Yang , Junfeng Niu . Covalently bonded ternary photocatalyst comprising MoSe2/black phosphorus nanosheet/graphitic carbon nitride for efficient moxifloxacin degradation. Chinese Chemical Letters, 2024, 35(9): 109453-. doi: 10.1016/j.cclet.2023.109453
Jiaojiao Liang , Youming Peng , Zhichao Xu , Yufei Wang , Menglong Liu , Xin Liu , Di Huang , Yuehua Wei , Zengxi Wei . Boron/phosphorus co-doped nitrogen-rich carbon nanofiber with flexible anode for robust sodium-ion battery. Chinese Chemical Letters, 2025, 36(1): 110452-. doi: 10.1016/j.cclet.2024.110452
Qiangqiang Zhou , Lili Sun , Yu-Jie Guo , Bo Zhou , Chunfang Zhang , Sen Xin , Le Yu , Gaohong Zhai . First-principles study on the electrochemical properties of Na-ion-intercalatable heterostructures formed by transitional metal dichalcogenides and blue phosphorus. Chinese Chemical Letters, 2025, 36(7): 110187-. doi: 10.1016/j.cclet.2024.110187
Xinyun Liu , Long Yuan , Xiaoli Peng , Shilan Li , Shengdong Jing , Shengjun Lu , Hua Lei , Yufei Zhang , Haosen Fan . MOF derived phosphorus doped cerium dioxide nanorods modified separator as efficient polysulfide barrier for advanced lithium-sulfur batteries. Chinese Chemical Letters, 2025, 36(10): 110369-. doi: 10.1016/j.cclet.2024.110369
Entian Cui , Yulian Lu , Zhaoxia Li , Zhilei Chen , Chengyan Ge , Jizhou Jiang . Interfacial B-O bonding modulated S-scheme B-doped N-deficient C3N4/O-doped-C3N5 for efficient photocatalytic overall water splitting. Chinese Chemical Letters, 2025, 36(1): 110288-. doi: 10.1016/j.cclet.2024.110288
Rongjian Chen , Jiahui Liu , Caixia Lin , Yuanming Li , Yanhou Geng , Yaofeng Yuan . Synthesis and properties of tetraphenylethene cationic cyclophanes based on o-carborane skeleton. Chinese Chemical Letters, 2024, 35(12): 110074-. doi: 10.1016/j.cclet.2024.110074
Lin Zhang , Jianlong Li , Maoyuan Hu , Yao Xu , Xiaoli Xiong , Zhaoyu Jin . MOF-derived beaded stream-like nitrogen and phosphorus-codoped carbon-coated Fe3O4 nanocomposites via lattice-oxygen-mediated mechanism for efficient water oxidation. Chinese Chemical Letters, 2025, 36(8): 111123-. doi: 10.1016/j.cclet.2025.111123