Synthesis, Table of Contents Synthesis 2020; 52(22): 3415-3419DOI: 10.1055/s-0040-1707346 special topic © Georg Thieme Verlag Stuttgart · New YorkCopper-Catalyzed Asymmetric Hydroamination of Styrenes with piv ZPhos as Ligand Authors Author Affiliations Chengsheng Chen Ling Wu Yuwen Wang Linglin Wu∗ Department of Chemical Development, Boehringer Ingelheim Pharmaceuticals, Inc., 900 Ridgebury Road/P.O. Box 368, Ridgefield, CT 06877-0368, USA Email: yongda.zhang@boehringer-ingelheim.com Email: linglin.wu@boehringer-ingelheim.com Yongda Zhang∗ Department of Chemical Development, Boehringer Ingelheim Pharmaceuticals, Inc., 900 Ridgebury Road/P.O. Box 368, Ridgefield, CT 06877-0368, USA Email: yongda.zhang@boehringer-ingelheim.com Email: linglin.wu@boehringer-ingelheim.com Recommend Article Abstract Buy Article(opens in new window) All articles of this category(opens in new window) Published as part of the Special Topic Synthesis in Industry Abstract A copper-catalyzed hydroamination of styrenes using piv ZPhos as ligand is reported. Enantioselectivities up to 94% are achieved under optimized conditions with aryl and heteroaryl styrenes. A variety of electrophilic O-benzoylhydroxylamines are well tolerated. Key words Key wordshydroamination - asymmetric catalysis - copper catalysis - styrene - phosphine ligand Full Text References References 1a Huang L, Arndt M, Gooßen K, Heydt H, Gooßen LJ. Chem. Rev. 2015; 115: 2596 1b Michon C, Abadie M.-A, Medina F, Agbossou-Niedercorn F. J. Organomet. Chem. 2017; 847: 13 2 Zhu S, Niljianskul N, Buchwald SL. J. Am. Chem. Soc. 2013; 135: 15746 3 Miki Y, Hirano K, Satoh T, Miura M. Angew. Chem. Int. Ed. 2013; 52: 10830 4a Bandar JS, Pirnot MT, Buchwald SL. J. Am. Chem. Soc. 2015; 137: 14812 4b Tobisch S. Chem. Eur. J. 2016; 22: 8290 5a Zhu S, Buchwald SL. J. Am. Chem. Soc. 2014; 136: 15913 5b Niu D, Buchwald SL. J. Am. Chem. Soc. 2015; 137: 9716 5c Zhu S, Niljianskul N, Buchwald SL. Nat. Chem. 2016; 8: 144 5d Miki Y, Hirano K, Satoh T, Miura M. Org. Lett. 2014; 16: 1498 5e Nishikawa D, Hirano K, Miura M. J. Am. Chem. Soc. 2015; 137: 15620 5f Xi Y, Butcher TW, Zhang J, Hartwig JF. Angew. Chem. Int. Ed. 2016; 55: 776 5g Liu RY, Buchwald SL. Acc. Chem. Res. 2020; 53: 1229 6 Yang Y, Shi SL, Niu D, Liu P, Buchwald SL. Science 2015; 349: 62 7 Xu G, Senanayake CH, Tang W. Acc. Chem. Res. 2019; 52: 1101 8 Chong E, Qu B, Zhang Y, Cannone ZP, Leung JC, Tcyrulnikov S, Nguyen KD, Haddad N, Biswas S, Hou X, Kaczanowska K, Chwalba M, Tracz A, Czarnocki S, Song JJ, Kozlowski MC, Senanayake CH. Chem. Sci. 2019; 10: 4339 9 Qu B, Tan R, Herling MR, Haddad N, Grinberg N, Kozlowski MC, Zhang X, Senanayake CH. J. Org. Chem. 2019; 84: 4915 10 Patel ND, Sieber JD, Tcyrulnikov S, Simmons BJ, Rivalti D, Duvvuri K, Zhang Y, Gao DA, Fandrick KR, Haddad N, Lao KS, Mangunuru HP. R, Biswas S, Qu B, Grinberg N, Pennino S, Lee H, Song JJ, Gupton BF, Garg NK, Kozlowski MC, Senanayake CH. ACS Catal. 2018; 8: 10190 11 Huang L, Zhu J, Jiao G, Wang Z, Yu X, Deng WP, Tang W. Angew. Chem. Int. Ed. 2016; 55: 4527 12 Du K, Guo P, Chen Y, Cao Z, Wang Z, Tang W. Angew. Chem. Int. Ed. 2015; 54: 3033 13 Zhang Y, Lao KS, Sieber JD, Xu Y, Wu L, Wang X.-J, Desrosiers J.-N, Lee H, Haddad N, Han ZS, Yee NK, Song JJ, Howell AR, Senanayake CH. Synthesis 2018; 50: 4429 14 Zatolochnaya OV, Rodríguez S, Zhang Y, Lao KS, Tcyrulnikov S, Li G, Wang XJ, Qu B, Biswas S, Mangunuru HP. R, Rivalti D, Sieber JD, Desrosiers JN, Leung JC, Grinberg N, Lee H, Haddad N, Yee NK, Song JJ, Kozlowski MC, Senanayake CH. Chem. Sci. 2018; 9: 4505 15 Wu L, Zatolochnaya O, Qu B, Wu L, Wells LA, Kozlowski MC, Senanayake CH, Song JJ, Zhang Y. Org. Lett. 2019; 21: 8952 16 Lipshutz BH, Noson K, Chrisman W, Lower A. J. Am. Chem. Soc. 2003; 125: 8779 17 Guo S, Yang JC, Buchwald SL. J. Am. Chem. Soc. 2018; 140: 15976 Supplementary Material Supplementary Material Supporting Information (PDF)
