Synlett 2021; 32(13): 1323-1329
DOI: 10.1055/a-1468-6136
cluster account
Perspectives on Organoheteroatom and Organometallic Chemistry

Manganese-Catalyzed C(sp2)–H Addition to Polar Unsaturated Bonds

Ting Liu
a   Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, CAS Research/Education Center for Excellence in Molecular Sciences, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, P. R. of China
b   University of Chinese Academy of Sciences, Beijing 100049, P. R. of China
,
Congyang Wang
a   Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, CAS Research/Education Center for Excellence in Molecular Sciences, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, P. R. of China
b   University of Chinese Academy of Sciences, Beijing 100049, P. R. of China
c   Physical Science Laboratory, Huairou National Comprehensive Science Center, Beijing 101400, P. R. of China
› Author Affiliations
Financial support from the National Natural Science Foundation of China (21772202, 21831008, 22025109), Beijing Municipal Science and Technology Commission (project No. Z191100007219009), Beijing National Laboratory for Molecular Sciences (BNLMS-CXXM-201901) and the K. C. Wong Education Foundation are gratefully acknowledged.


Abstract

Transition-metal-catalyzed nucleophilic C–H addition of hydrocarbons to polar unsaturated bonds could intrinsically avoid prefunctionalization of substrates and formation of waste byproducts, thus featuring high step- and atom-economy. As the third most abundant transition metal, manganese-catalyzed C–H addition to polar unsaturated bonds remains challenging, partially due to the difficulty in building a closed catalytic cycle of manganese. In the past few years, we have developed manganese catalysis to enable the sp2-hydrid C–H addition to polar unsaturated bonds (e.g., imines, aldehydes, nitriles), which will be discussed in this personal account.

1 Introduction

2 Mn-Catalyzed N-Directed C(sp2)–H Addition to Polar Unsaturated Bonds

3 Mn-Catalyzed O-Directed C(sp2)–H Addition to Polar Unsaturated Bonds

4 Conclusion



Publication History

Received: 23 February 2021

Accepted after revision: 27 March 2021

Accepted Manuscript online:
27 March 2021

Article published online:
28 April 2021

© 2021. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 
  • References

  • 1 Zhang X.-S, Chen K, Shi Z.-J. Chem. Sci. 2014; 5: 2146
  • 2 Yang L, Huang H. Chem. Rev. 2015; 115: 3468
  • 3 Hummel JR, Boerth JA, Ellman JA. Chem. Rev. 2017; 117: 9163
  • 4 Gandeepan P, Muller T, Zell D, Cera G, Warratz S, Ackermann L. Chem. Rev. 2019; 119: 2192
  • 5 Wang C. Synlett 2013; 24: 1606
  • 6 Liu W, Groves JT. Acc. Chem. Res. 2015; 48: 1727
  • 7 Liu W, Ackermann L. ACS Catal. 2016; 6: 3743
  • 8 Valyaev DA, Lavigne G, Lugan N. Coord. Chem. Rev. 2016; 308: 191
  • 9 Carney JR, Dillon BR, Thomas SP. Eur. J. Org. Chem. 2016; 3912
  • 10 Hu Y, Zhou B, Wang C. Acc. Chem. Res. 2018; 51: 816
  • 11 Wang Z, Chen L, Mao G, Wang C. Chin. Chem. Lett. 2020; 31: 1890
  • 12 Bruce MI, Iqbal MZ, Stone FG. A. J. Chem. Soc. A 1970; 3204
  • 13 Zhou B, Chen H, Wang C. J. Am. Chem. Soc. 2013; 135: 1264
  • 14 He R, Huang ZT, Zheng QY, Wang C. Angew. Chem. Int. Ed. 2014; 53: 4950
  • 15 Zhou B, Ma P, Chen H, Wang C. Chem. Commun. 2014; 50: 14558
  • 16 Yang X, Jin X, Wang C. Adv. Synth. Catal. 2016; 358: 2436
  • 17 Hu Y, Wang C. Sci. China Chem. 2016; 59: 1301
  • 18 Hu Y, Zhou B, Chen H, Wang C. Angew. Chem. Int. Ed. 2018; 57: 12071
  • 19 Ali S, Huo J, Wang C. Org. Lett. 2019; 21: 6961
  • 20 Hu Y, Wang C. ChemCatChem 2019; 11: 1167
  • 21 Jia T, Wang C. ChemCatChem 2019; 11: 5292
  • 22 Wang Z, Wang C. Green Synth. Catal. 2021; 2: 66
  • 23 Kuninobu Y, Nishina Y, Takeuchi T, Takai K. Angew. Chem. Int. Ed. 2007; 46: 6518
  • 24 Zhou B, Hu Y, Wang C. Angew. Chem. Int. Ed. 2015; 54: 13659
  • 25 Liu W, Bang J, Zhang Y, Ackermann L. Angew. Chem. Int. Ed. 2015; 54: 14137
  • 26 Liang YF, Massignan L, Liu W, Ackermann L. Chem. Eur. J. 2016; 22: 14856
  • 27 Liang Y.-F, Massignan L, Ackermann L. ChemCatChem 2018; 10: 2768
  • 28 Liu W, Richter SC, Mei R, Feldt M, Ackermann L. Chem. Eur. J. 2016; 22: 17958
  • 29 Yu X, Tang J, Jin X, Yamamoto Y, Bao M. Asian J. Org. Chem. 2018; 7: 550
  • 30 Wang C, Maity B, Cavallo L, Rueping M. Org. Lett. 2018; 20: 3105
  • 31 Kong X, Lin L, Xu B. Adv. Synth. Catal. 2018; 360: 2801
  • 32 Kong X, Xu B. Asian J. Org. Chem. 2019; 8: 1862
  • 33 Zhou X, Li Z, Zhang Z, Lu P, Wang Y. Org. Lett. 2018; 20: 1426
  • 34 Xu Z, Wang Y, Zheng Y, Huang Z, Ackermann L, Ruan Z. Org. Chem. Front. 2020; 7: 3709
  • 35 Zheng Q.-Z, Jiao N. Tetrahedron Lett. 2014; 55: 1121
  • 36 Huang Z, Lim HN, Mo F, Young MC, Dong G. Chem. Soc. Rev. 2015; 44: 7764
  • 37 Sueki S, Wang Z, Kuninobu Y. Org. Lett. 2016; 18: 304
  • 38 McKinney RJ, Firestein G, Kaesz HD. Inorg. Chem. 1975; 14: 2057
  • 39 Zhou B, Hu Y, Liu T, Wang C. Nat. Commun. 2017; 8: 1169
  • 40 Kong X, Xu B. Org. Lett. 2018; 20: 4495
  • 41 Liu T, Hu Y, Yang Y, Wang C. CCS Chem. 2020; 2: 749