Synlett 2019; 30(09): 1008-1014
DOI: 10.1055/s-0037-1612214
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© Georg Thieme Verlag Stuttgart · New York

Enantioselective Reductive Diarylation of Alkenes by Ni-Catalyzed Domino Heck Cyclization/Cross Coupling

Kuai Wang
,
The Center for Precision Synthesis, Institute for Advanced Studies, Wuhan University, Wuhan, 430072, P. R. of China   Email: wqkong@whu.edu.cn
› Author Affiliations
We acknowledge financial support from the ‘1000-Youth Talents Plan’, National Natural Science Foundation of China (No. 21702149) and Fundamental Research Funds for the Central Universities (2042018kf0012).
Further Information

Publication History

Received: 19 December 2018

Accepted after revision: 21 January 2019

Publication Date:
18 February 2019 (online)


Abstract

A Ni-catalyzed enantioselective reductive diarylation of alkenes through a tandem Heck cyclization/cross coupling of two structurally distinguished aryl bromides is accomplished for the first time. This reaction takes place under very mild conditions with high efficiency and tolerates a variety of functional groups. Thus, it provides a rapid access to various medicinally relevant bis-heterocycles containing all-carbon quaternary centers with very high enantioselectivity.

 
  • References


    • For selected reviews on alkene diarylation, see:
    • 1a Zeni G, Larock RC. Chem. Rev. 2006; 106: 4644
    • 1b DeLuca RJ, Stokes BJ, Sigman MS. Pure Appl. Chem. 2014; 86: 395
    • 1c Giri R, KC S. J. Org. Chem. 2018; 83: 3013
    • 1d Ping Y, Li Y, Zhu J, Kong W. Angew. Chem. Int. Ed. 2019; 58: 1562
    • 1e Dhungana RK, KC S, Basnet P, Giri R. Chem. Rec. 2018; 18: 1314 and references therein
  • 2 Stokes JB, Liao L, de Andrade AM, Wang Q, Sigman MS. Org. Lett. 2014; 16: 4666
  • 3 You W, Brown MK. J. Am. Chem. Soc. 2015; 137: 14578

    • For selected examples on Pd-catalyzed oxidative diarylation of alkenes, see:
    • 4a Urkalan KB, Sigman MS. Angew. Chem. Int. Ed. 2009; 48: 3146
    • 4b Trejos A, Odell LR, Larhed M. ChemistryOpen 2012; 1: 49

      For selected examples on Pd-catalyzed alkene 1,2-diarylation, see:
    • 5a Seashore-Ludlow B, Somfai P. Org. Lett. 2012; 14: 3858
    • 5b Wilson JE. Tetrahedron Lett. 2012; 53: 2308
    • 5c Saini V, Sigman MS. J. Am. Chem. Soc. 2012; 134: 11372
    • 5d Liu Z, Zeng T, Yang KS, Engle KM. J. Am. Chem. Soc. 2016; 138: 15122
    • 5e Petrone DA, Kondo M, Zeidan N, Lautens M. Chem. Eur. J. 2016; 22: 5684

      For references on Ni-catalyzed alkene diarylation, see:
    • 6a Shrestha B, Basnet P, Dhungana RK, KC S, Thapa S, Sears JM, Giri R. J. Am. Chem. Soc. 2017; 139: 10653
    • 6b Li W, Boon JK, Zhao Y. Chem. Sci. 2018; 9: 600
    • 6c Derosa J, Tran VT, Boulous MN, Chen JS, Engle KM. J. Am. Chem. Soc. 2017; 139: 10657
    • 7a You W, Brown MK. J. Am. Chem. Soc. 2014; 136: 14730
    • 7b Wang F, Wang D, Wan X, Wu L, Chen P, Liu G. J. Am. Chem. Soc. 2016; 138: 15547
    • 7c Wu L, Wang F, Wan X, Wang D, Chen P, Liu G. J. Am. Chem. Soc. 2017; 139: 2904

      For reviews on Ni-catalyzed reductive cross-coupling reactions, see:
    • 8a Nédélec J.-Y, Périchon J, Troupel M. Top. Curr. Chem. 1997; 185: 141
    • 8b Knappke CE. I, Grupe S, Gärtner D, Corpet M, Gosmini C, Jacobi von Wangelin A. Chem. Eur. J. 2014; 20: 6828
    • 8c Moragas T, Correa A, Martin R. Chem. Eur. J. 2014; 20: 8242
    • 8d Everson DA, Weix DJ. J. Org. Chem. 2014; 79: 4793
    • 8e Tasker SZ, Standley EA, Jamison TF. Nature 2014; 509: 299
    • 8f Gu J, Wang X, Xue W, Gong H. Org. Chem. Front. 2015; 2: 1411
    • 8g Tollefson EJ, Hanna LE, Jarvo ER. Acc. Chem. Res. 2015; 48: 2344
    • 8h Weix DJ. Acc. Chem. Res. 2015; 48: 1767
    • 8i Cherney AH, Kadunce NT, Reisman SE. Chem. Rev. 2015; 115: 9587
    • 8j Wang X, Dai Y, Gong H. Top Curr. Chem. (Z) 2016; 374: 43
    • 8k Lucas EL, Jarvo ER. Nat. Rev. Chem. 2017; 1: 65
    • 8l Richmond E, Moran J. Synthesis 2018; 50: 499 ; and references therein
    • 9a Kong W, Wang Q, Zhu J. J. Am. Chem. Soc. 2015; 137: 16028
    • 9b Kong W, Wang Q, Zhu J. Angew. Chem. Int. Ed. 2017; 56: 3987
    • 9c Li Y, Wang K, Ping Y, Wang Y, Kong W. Org. Lett. 2018; 20: 921
  • 10 Wang K, Ding Z, Zhou Z, Kong W. J. Am. Chem. Soc. 2018; 140: 12364
    • 11a Cummings SP, Le T.-N, Fernandez GE, Quiambao LG, Stokes BJ. J. Am. Chem. Soc. 2016; 138: 6107
    • 11b Xuan Q, Song Q. Org. Lett. 2016; 18: 4250
    • 11c Ojha DP, Gadde K, Prabhu KR. Org. Lett. 2016; 18: 5062
    • 11d Shirakawa E, Takahashi G, Tsuchimoto T, Kawakami Y. Chem. Commun. 2001; 2688

      For references on alkyl-Ni(II) complexes, see:
    • 12a Jones GD, Martin J, McFarland C, Allen O, Hall R, Haley A, Brandon R, Konovalova T, Desrochers P, Pulay P, Vicic D. J. Am. Chem. Soc. 2006; 128: 13175
    • 12b Csok Z, Vechorkin O, Harkins SB, Scopelliti R, Hu X. J. Am. Chem. Soc. 2008; 130: 8156
    • 13a Everson DA, Jones BA, Weix DJ. J. Am. Chem. Soc. 2012; 134: 6146
    • 13b Biswas S, Weix DJ. J. Am. Chem. Soc. 2013; 135: 16192
    • 13c Ackerman LK. G, Lovell MM, Weix DJ. Nature 2015; 524: 454