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

Herein, we report the divergent synthesis of alkynylated imidazo­[1,5-a]­indoles and α,α-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 selectivit...

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Bibliographic Details
Published inOrganic letters Vol. 23; no. 15; pp. 5766 - 5771
Main Authors Zhao, Fei, Qiao, Jin, Lu, Yangbin, Zhang, Xiaoning, Dai, Long, Gong, Xin, Mao, Hui, Lu, Shiyao, Wu, Xiaowei, Liu, Siyu
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 06.08.2021
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ACTIVATION
DESIGN
ANNULATION
ACIDS
C2-ALKENYLATION
ALKYNES
CLEAVAGE
DERIVATIVES
INDOLES
ALKENYLATION
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Summary:Herein, we report the divergent synthesis of alkynylated imidazo­[1,5-a]­indoles and α,α-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.
Bibliography:ObjectType-Article-1
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content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.1c01929