Redox-Neutral Rhodium(III)-Catalyzed Chemospecific and Regiospecific [4+1] Annulation between Indoles and Alkenes for the Synthesis of Functionalized Imidazo[1,5‑a]indoles

Exploiting internal alkenes embedded with an oxidizing function/leaving group as a rare and unconventional one-carbon unit, a redox-neutral rhodium­(III)-catalyzed chemo- and regiospecific [4+1] annulation between indoles and alkenes for the synthesis of functionalized imidazo­[1,5-a]­indoles has be...

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Published inJournal of organic chemistry Vol. 86; no. 15; pp. 10591 - 10607
Main Authors Zhao, Fei, Qiao, Jin, Lu, Yangbin, Zhang, Xiaoning, Dai, Long, Liu, Siyu, Ni, Hangcheng, Jia, Xiuwen, Wu, Xiaowei, Lu, Shiyao
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 06.08.2021
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
TRACELESS DIRECTING GROUP
O BOND
NATURAL-PRODUCTS
EFFICIENT SYNTHESIS
REGIOSELECTIVE SYNTHESIS
N BOND
BOND ACTIVATION
DIAZO-COMPOUNDS
ALPHA,BETA-UNSATURATED KETOXIMES
C-H ACTIVATION
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Summary:Exploiting internal alkenes embedded with an oxidizing function/leaving group as a rare and unconventional one-carbon unit, a redox-neutral rhodium­(III)-catalyzed chemo- and regiospecific [4+1] annulation between indoles and alkenes for the synthesis of functionalized imidazo­[1,5-a]­indoles has been achieved. Internal alkenes employed here can fulfill an unusual [4+1] annulation rather than normal [4+2] annulation/C–H alkenylation. This method is characterized by excellent chemo- and regioselectivity, broad substrate scope, good functional group tolerance, good to high yields, and redox-neutral conditions.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.1c01256