4.8 Article

Rh(III)-Catalyzed Divergent Synthesis of Alkynylated Imidazo[1,5-a]indoles and α,α-Difluoromethylene Tetrasubstituted Alkenes

Journal

ORGANIC LETTERS
Volume 23, Issue 15, Pages 5766-5771

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c01929

Keywords

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Funding

  1. Natural Science Foundation of Zhejiang Province [LQ19B020003, LY21B020003]
  2. National Natural Science Foundation of China [21602022]
  3. Chengdu Talents Program
  4. 1000 Talents Program of Sichuan Province
  5. Longquanyi District Talents Program
  6. Science and Technology Program of Sichuan Province [2018JY0345]
  7. Jinhua Branch of Sichuan Industrial Institute of Antibiotics [1003]
  8. Chengdu University [2081915037]

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In this study, alkynylated imidazo[1,5-a]indoles and alpha,alpha-difluoromethylene tetrasubstituted alkenes were successfully synthesized via Rh(III)-catalyzed [4 + 1] annulation/alkyne moiety migration and C-H alkenylation/DG migration, showing excellent product selectivity, high yields, and good tolerance of functional groups.
Herein, we report the divergent synthesis of alkynylated imidazo[1,5-a]indoles and alpha,alpha-difluoromethylene tetrasubstituted alkenes through Rh(III)-catalyzed [4 + 1] annulation/alkyne moiety migration and C-H alkenylation/DG migration, respectively. This protocol features tunable product selectivity, excellent chemo-, regio-, and stereoselectivity, broad substrate scope, moderate to high yields, good tolerance of functional groups, and mild redox-neutral conditions.

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