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Synlett 2022; 33(03): 224-230
DOI: 10.1055/a-1637-9308
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Nickel Hydride Catalyzed Remote Hydroarylation of Olefins

Yuli He  ‡
a   State Key Laboratory of Coordination Chemistry, Chemistry and Biomedicine Innovation Center (ChemBIC), Jiangsu Key Laboratory of Advanced Organic Materials, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210093, P. R. of China
,
Ran Tao‡
a   State Key Laboratory of Coordination Chemistry, Chemistry and Biomedicine Innovation Center (ChemBIC), Jiangsu Key Laboratory of Advanced Organic Materials, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210093, P. R. of China
b   Department of Chemistry, New York University, New York, 10003, USA
,
Shaolin Zhu  ∗
a   State Key Laboratory of Coordination Chemistry, Chemistry and Biomedicine Innovation Center (ChemBIC), Jiangsu Key Laboratory of Advanced Organic Materials, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210093, P. R. of China
› Author AffiliationsSupport was provided by the National Natural Science Foundation of China (NSFC, Gran Numbers 21772087 and 22001118) and the Natural Science Foundation of Jiangsu Province (Grant Number BK20200300).
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Abstract

Metal hydride catalyzed remote hydrofunctionalization has attracted extensive attention in the past decade, as it provides a complementary approach for selective functionalization of remote C(sp3)–H bonds. Recently, a wide variety of olefinic remote hydrofunctionalization reactions have been realized through the synergistic combination of NiH-catalyzed chain-walking and Ni-catalyzed cross-coupling. In this Account we discuss our recent achievements in the remote hydroarylation of olefins and in asymmetric hydroarylation.

1 Introduction

2 NiH-Catalyzed Remote Hydroarylation

3 Progress in Asymmetric Catalysis

4 Conclusion

Key words

nickel catalysis - nickel hydride - chain-walking - C–H functionalization - hydroarylation - alkene - asymmetric catalysis


Publication History

Received: 20 August 2021

Accepted after revision: 06 September 2021

Accepted Manuscript online:
06 September 2021

Article published online:
24 September 2021

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  • References and Notes

  • 1 Saint-Denis TG, Zhu R.-Y, Chen G, Wu Q.-F, Yu J.-Q. Science 2018; 359: eaao4798
    CrossrefPubMed

      • For selected reviews on metal hydride chemistry, see:
    • 2a Pirnot MT, Wang Y.-M, Buchwald SL. Angew. Chem. Int. Ed. 2016; 55: 48
      CrossrefPubMed
    • 2b Nguyen KD, Park BY, Luong T, Sato H, Garza VJ, Krische MJ. Science 2016; 354: 300
      CrossrefPubMed
    • 2c Eberhardt NA, Guan H. Chem. Rev. 2016; 116: 8373
      CrossrefPubMed
    • 2d Crossley SW. M, Obradors C, Martinez RM, Shenvi RA. Chem. Rev. 2016; 116: 8912
      CrossrefPubMed
    • 2e Chen J, Guo J, Lu Z. Chin. J. Chem. 2018; 36: 1075
      Crossref
    • 2f Wang X.-X, Lu X, Li Y, Wang J.-W, Fu Y. Sci. China Chem. 2020; 63: 1586
      Crossref

      For reviews on remote functionalization via chain-walking, see:
    • 3a Larionov E, Li H, Mazet C. Chem. Commun. 2014; 50: 9816
      CrossrefPubMed
    • 3b Vasseur A, Bruffaerts J, Marek I. Nat. Chem. 2016; 8: 209
      CrossrefPubMed
    • 3c Sommer H, Juliá-Hernández F, Martin R, Marek I. ACS Cent. Sci. 2018; 4: 153
      CrossrefPubMed
    • 3d Janssen-Müller D, Sahoo B, Sun S.-Z, Martin R. Isr. J. Chem. 2020; 60: 195
      Crossref

      For selected reviews on nickel catalysis, see:
    • 4a Netherton MR, Fu GC. Adv. Synth. Catal. 2004; 346: 1525
      Crossref
    • 4b Hu X. Chem. Sci. 2011; 2: 1867
      CrossrefPubMed
    • 4c Montgomery J. Organonickel Chemistry . In Organometallics in Synthesis . Lipshutz BH. John Wiley & Sons; Hoboken: 2013: 319-428
      CrossrefGoogle Scholar
    • 4d Tasker SZ, Standley EA, Jamison TF. Nature 2014; 509: 299
      CrossrefPubMed
    • 4e Nickel Catalysis in Organic Synthesis . Ogoshi S. Wiley-VCH; Weinheim: 2020
      Google Scholar
    • 4f Poremba KE, Dibrell SE, Reisman SE. ACS Catal. 2020; 10: 8237
      CrossrefPubMed
  • 5 Busolv I, Becouse J, Mazza S, Montandon-Clerc M, Hu X. Angew. Chem. Int. Ed. 2015; 54: 14523
    CrossrefPubMed
    • 6a Lee W.-C, Wang C.-H, Lin Y.-H, Shih W.-C, Ong T.-G. Org. Lett. 2013; 15: 5358
      CrossrefPubMed
    • 6b Bair JS, Schramm Y, Sergeev AG, Clot E, Eisenstein O, Hartwig JF. J. Am. Chem. Soc. 2014; 136: 13098
      CrossrefPubMed
    • 6c He Y, Cai Y, Zhu S. J. Am. Chem. Soc. 2017; 139: 1061
      CrossrefPubMed
    • 6d Chen F, Chen K, Zhang Y, He Y, Wang Y.-M, Zhu S. J. Am. Chem. Soc. 2017; 139: 13929
      CrossrefPubMed
    • 6e Peng L, Yin G. Org. Lett. 2018; 20: 1880
      CrossrefPubMed
    • 6f Zhang Y, Han B, Zhu S. Angew. Chem. Int. Ed. 2019; 58: 13860
      CrossrefPubMed
    • 6g Kumar GS, Peshkov A, Brzozowska A, Nikolaienko P, Zhu C, Rueping M. Angew. Chem. Int. Ed. 2020; 59: 6513
      CrossrefPubMed
    • 6h He Y, Liu C, Yu L, Zhu S. Angew. Chem. Int. Ed. 2020; 59: 9186
      CrossrefPubMed
    • 6i He Y, Han B, Zhu S. Organometallics 2021; 40: 2253
      Crossref
    • 7a Zhou F, Zhu J, Zhang Y, Zhu S. Angew. Chem. Int. Ed. 2018; 57: 4058
      CrossrefPubMed
    • 7b Wang Z.-Y, Wan J.-H, Wang G.-Y, Wang R, Jin R.-X, Lan Q, Wang X.-S. Tetrahedron Lett. 2018; 59: 2302
      Crossref
    • 7c Sun S.-Z, Börjesson M, Martin-Montero R, Martin R. J. Am. Chem. Soc. 2018; 140: 12765
      CrossrefPubMed
    • 7d Wang Z, Yin H, Fu GC. Nature 2018; 563: 379
      CrossrefPubMed
    • 7e Zhou F, Zhang Y, Xu X, Zhu S. Angew. Chem. Int. Ed. 2019; 58: 1754
      CrossrefPubMed
    • 7f Qian D, Hu X. Angew. Chem. Int. Ed. 2019; 58: 18519
      CrossrefPubMed
    • 7g Sun S.-Z, Romano C, Martin R. J. Am. Chem. Soc. 2019; 141: 16197
      CrossrefPubMed
    • 8a Juliá-Hernández F, Moragas T, Cornella J, Martin R. Nature 2017; 545: 84
      CrossrefPubMed
    • 8b Gaydou M, Moragas T, Juliá-Hernández F, Martin R. J. Am. Chem. Soc. 2017; 139: 12161
      CrossrefPubMed
  • 9 Liu J, Gong H, Zhu S. Angew. Chem. Int. Ed. 2021; 60: 4060
    CrossrefPubMed
  • 10 Jiang X, Han B, Xue Y, Duan M, Gui Z, Wang Y, Zhu S. Nat. Commun. 2021; 12: 3792
    CrossrefPubMed
  • 11 He J, Song P, Xu X, Zhu S, Wang Y. ACS Catal. 2019; 9: 3253
    Crossref
    • 12a Xiao J, He Y, Ye F, Zhu S. Chem 2018; 4: 1645
      CrossrefPubMed
    • 12b Zhang Y, He J, Song P, Wang Y, Zhu S. CCS Chem. 2020; 2: 2259
  • 13 Zhang Y, Xu X, Zhu S. Nat. Commun. 2019; 10: 1752
    CrossrefPubMed
  • 14 Yu R, Rajasekar S, Fang X. Angew. Chem. Int. Ed. 2020; 59: 21436
    CrossrefPubMed
  • 15 Chain walking may also be catalyzed by Ni(II)H species, see ref. 7d and 8a.
  • 16 Bera S, Hu X. Angew. Chem. Int. Ed. 2019; 58: 13854
    CrossrefPubMed
  • 17 Lu X, Xiao B, Zhang Z, Gong T, Su W, Fu Y, Liu L. Nat. Commun. 2016; 7: 11129
    CrossrefPubMed
  • 18 Jiao K.-J, Liu D, Ma H.-X, Qiu H, Fang P, Mei T.-S. Angew. Chem. Int. Ed. 2020; 59: 6520
    CrossrefPubMed
  • 19 Iwamoto H, Tsuruta T, Ogoshi S. ACS Catal. 2021; 11: 6741
    Crossref
  • 20 Lv X.-Y, Fan C, Xiao L.-J, Xie J.-H, Zhou Q.-L. CCS Chem. 2019; 1: 328
    Crossref
  • 21 Chen Y.-G, Shuai B, Xu X.-T, Li Y.-Q, Yang Q.-L, Qiu H, Zhang K, Fang P, Mei T.-S. J. Am. Chem. Soc. 2019; 141: 3395
    CrossrefPubMed
  • 22 Cheng Q, Dang Y. Org. Lett. 2020; 22: 8998
    CrossrefPubMed
    • 23a He Y, Liu C, Yu L, Zhu S. Angew. Chem. Int. Ed. 2020; 59: 21530
      CrossrefPubMed
    • 23b Cuesta-Galisteo S, Schörgenhumer J, Wei X, Merino E, Nevado C. Angew. Chem. Int. Ed. 2021; 60: 1605
      CrossrefPubMed
    • 23c He Y, Song H, Zhu S. Nat. Commun. 2021; 12: 638
      CrossrefPubMed
  • 24 For intramolecular version, see: Zhang W.-B, Yang X.-T, Ma J.-B, Su Z.-M, Shi S.-L. J. Am. Chem. Soc. 2019; 141: 5628
    CrossrefPubMed
  • 25 For synergistic CuH/Pd-catalyzed asymmetric hydroarylation, see: Friis SD, Pirnot MT, Buchwald SL. J. Am. Chem. Soc. 2016; 138: 8372
    CrossrefPubMed
    • 26a Zhu S, Niljianskul N, Buchwald SL. J. Am. Chem. Soc. 2013; 135: 15746
      CrossrefPubMed
    • 26b Miki Y, Hirano K, Satoh T, Miura M. Angew. Chem. Int. Ed. 2013; 52: 10830
      CrossrefPubMed
  • 27 Chen F, Zhang Y, Yu L, Zhu S. Angew. Chem. Int. Ed. 2017; 56: 2022
    CrossrefPubMed