Synthesis, Table of Contents Synthesis 2023; 55(16): 2586-2594DOI: 10.1055/a-2067-4165 paper Special Issue Honoring Prof. Guoqiang Lin’s Contributions to Organic Chemistry Synthesis of Triarylphosphines via Cu-Catalyzed Coupling of Aryl Halides and Acylphosphines Minghui Xu , Zhengping Zhu , Haojie Yi , Hong Zhu∗ , Zhiqian Wang ∗ Recommend Article Abstract Buy Article All articles of this category Dedicated to Professor Guo-Qiang Lin on the occasion of his 80th birthday Abstract A Cu-catalyzed C(sp2)–P bond forming reaction using an acylphosphine as the phosphorus source is reported; with CuCl2 as the catalyst, 34 examples of aryl iodides and bromides were converted into triarylphosphines in good to excellent yield. A preliminary study of the mechanism was carried out and found that a radical intermediate is not involved. This reaction is an extension of the application of acylphosphines in Cu-catalyzed reactions and shows their potential as a phosphination reagent in the synthesis of tertiary phosphines. Key words Key wordsCu catalysis - acylphosphines - C(sp2)–P bond formation - triarylphosphine - phosphination reagent Full Text References References 1a Jiang T, Zhang H, Ding Y, Zou S, Chang R, Huang H. Chem. Soc. Rev. 2020; 49: 1487 1b Surry DS, Buchwald SL. Angew. Chem. Int. Ed. 2008; 47: 6338 1c Xie J.-H, Zhou Q.-L. Acc. Chem. Res. 2008; 41: 581 1d Yang J, Chen X, Wang Z. Tetrahedron Lett. 2015; 56: 5673 2a Fernández-Pérez H, Etayo P, Panossian A, Vidal-Ferran A. Chem. Rev. 2011; 111: 2119 2b Genet J.-P, Ayad T, Ratovelomanana-Vidal V. Chem. Rev. 2014; 114: 2824 2c Xie C, Smaligo AJ, Song X.-R, Kwon O. ACS Cent. Sci. 2021; 7: 536 2d Zhang W, Chi Y, Zhang X. Acc. Chem. Res. 2007; 40: 1278 2e Zheng S, Lu X. Org. Lett. 2009; 11: 3978 3a Balueva AS, Musina EI, Karasik AA. Phosphines: Preparation, Reactivity and Applications . In Organophosphorus Chemistry, Vol. 47. The Royal Society of Chemistry; Cambridge: 2018: 1-49 3b Li J, Yang C, Bai Y, Yang X, Liu Y, Peng J. J. Organomet. Chem. 2018; 855: 7 3c Montchamp J.-L. Acc. Chem. Res. 2014; 47: 77 3d Padmaperuma AB, Sapochak LS, Burrows PE. Chem. Mater. 2006; 18: 2389 3e Queffélec C, Petit M, Janvier P, Knight DA, Bujoli B. Chem. Rev. 2012; 112: 3777 3f Wendels S, Chavez T, Bonnet M, Salmeia KA, Gaan S. Materials 2017; 10: 784 4a Wang L, Chen H, Duan Z. Chem. Asian J. 2018; 13: 2164 4b Chen T, Tan Q, Liu X, Liu L, Huang T, Han L.-B. Synthesis 2021; 53: 95 4c Arisawa M. Synthesis 2020; 52: 2795 5a Chen X, Liu X, Zhu H, Wang Z. Tetrahedron 2021; 81: 131912 5b Isshiki R, Muto K, Yamaguchi J. Org. Lett. 2018; 20: 1150 5c Liu C, Szostak M. Angew. Chem. Int. Ed. 2017; 56: 12718 5d Rout L, Punniyamurthy T. Coord. Chem. Rev. 2021; 431: 213675 5e Yu R, Chen X, Martin SF, Wang Z. Org. Lett. 2017; 19: 1808 6a Hu G, Shan C, Chen W, Xu P, Gao Y, Zhao Y. Org. Lett. 2016; 18: 6066 6b Liu X.-Y, Zou Y.-X, Ni H.-L, Zhang J, Dong H.-B, Chen L. Org. Chem. Front. 2020; 7: 980 6c Zhang H, Li W, Zhu C. J. Org. Chem. 2017; 82: 2199 6d Zhang H, Zhang X.-Y, Dong D.-Q, Wang Z.-L. RSC Adv. 2015; 5: 52824 6e Li Y.-B, Tian H, Zhang S, Xiao J.-Z, Yin L. Angew. Chem. Int. Ed. 2022; 61: e202117760 6f Zhang S, Xiao J.-Z, Li Y.-B, Shi C.-Y, Yin L. J. Am. Chem. Soc. 2021; 143: 9912 6g Li Y.-B, Tian H, Yin L. J. Am. Chem. Soc. 2020; 142: 20098 6h Yue W.-J, Xiao J.-Z, Zhang S, Yin L. Angew. Chem. Int. Ed. 2020; 59: 7057 7a Allen DV, Venkataraman D. J. Org. Chem. 2003; 68: 4590 7b Chao Z, Ma M, Gu Z. Org. Lett. 2020; 22: 6441 7c Gelman D, Jiang L, Buchwald SL. Org. Lett. 2003; 5: 2315 7d Li C.-J, Lü J, Zhang Z.-X, Zhou K, Li Y, Qi G.-H. Res. Chem. Intermed. 2018; 44: 4547 7e Tani K, Behenna DC, McFadden RM, Stoltz BM. Org. Lett. 2007; 9: 2529 7f Chen Q, Yan X, Wen C, Zeng J, Huang Y, Liu X, Zhang K. J. Org. Chem. 2016; 81: 9476 7g Huang C, Tang X, Fu H, Jiang Y, Zhao Y. J. Org. Chem. 2006; 71: 5020 7h Ke J, Tang Y, Yi H, Li Y, Cheng Y, Liu C, Lei A. Angew. Chem. Int. Ed. 2015; 54: 6604 7i Yu Y, Yi S, Zhu C, Hu W, Gao B, Chen Y, Wu W, Jiang H. Org. Lett. 2016; 18: 400 7j Zhou A.-X, Mao L.-L, Wang G.-W, Yang S.-D. Chem. Commun. 2014; 50: 8529 7k Zhuang R, Xu J, Cai Z, Tang G, Fang M, Zhao Y. Org. Lett. 2011; 13: 2110 7l Imamoto T, Kikuchi S.-i, Miura T, Wada Y. Org. Lett. 2001; 3: 87 7m Imamoto T, Oshiki T, Onozawa T, Kusumoto T, Sato K. J. Am. Chem. Soc. 1990; 112: 5244 7n Li Y, Das S, Zhou S, Junge K, Beller M. J. Am. Chem. Soc. 2012; 134: 9727 7o Li Y, Lu L.-Q, Das S, Pisiewicz S, Junge K, Beller M. J. Am. Chem. Soc. 2012; 134: 18325 7p Wu H.-C, Yu J.-Q, Spencer JB. Org. Lett. 2004; 6: 4675 8a Chen X, Wu H, Yu R, Zhu H, Wang Z. J. Org. Chem. 2021; 86: 8987 8b Yang J, Wu H, Wang Z. J. Saudi Chem. Soc. 2018; 22: 1 8c Yu R, Chen X, Wang Z. Tetrahedron Lett. 2016; 57: 3404 8d Zhang M, Ma Z, Du H, Wang Z. Tetrahedron Lett. 2020; 61: 152125 9a Bunnett JF, Creary X. J. Org. Chem. 1974; 39: 3611 9b Cristau H.-J, Cellier PP, Spindler J.-F, Taillefer M. Chem. Eur. J. 2004; 10: 5607 9c He C, Guo S, Huang L, Lei A. J. Am. Chem. Soc. 2010; 132: 8273 9d Bowman WR, Heaney H, Smith PH. G. Tetrahedron Lett. 1984; 25: 5821 9e Paine AJ. J. Am. Chem. Soc. 1987; 109: 1496 10 Tang Y.-P, Luo Y.-E, Xiang J.-F, He Y.-M, Fan Q.-H. Angew. Chem. Int. Ed. 2022; 61: e202200638 11 Xue M, Li J, Peng J, Bai Y, Zhang G, Xiao W, Lai G. Appl. Organomet. Chem. 2014; 28: 120 12 Guo R, Sang J, Xiao H, Li J, Zhang G. Chin. J. Chem. 2022; 40: 1337 13 Le Gall E, Aïssi KB, Lachaise I, Troupel M. Synlett 2006; 954 Supplementary Material Supplementary Material Supporting Information
