Synthesis 2020; 52(22): 3415-3419
DOI: 10.1055/s-0040-1707346
special topic
© Georg Thieme Verlag Stuttgart · New York

Copper-Catalyzed Asymmetric Hydroamination of Styrenes with piv ZPhos as Ligand

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
› Author Affiliations
We thank Boehringer Ingelheim Pharmaceuticals for financial support.
Further Information

Publication History

Received: 15 May 2020

Accepted after revision: 19 June 2020

Publication Date:
06 August 2020 (online)


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.

Supporting Information

 
  • 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