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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

Zhao, Fei; Qiao, Jin; Lu, Yangbin; Zhang, Xiaoning; Dai, Long; Liu, Siyu; Ni, Hangcheng; ... Lu, Shiyao; + view all (2021) 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. The Journal of Organic Chemistry , 86 (15) pp. 10591-10607. 10.1021/acs.joc.1c01256. Green open access

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Abstract

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.

Type: Article
Title: 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
Location: United States
Open access status: An open access version is available from UCL Discovery
DOI: 10.1021/acs.joc.1c01256
Publisher version: https://doi.org/10.1021/acs.joc.1c01256
Language: English
Additional information: This version is the author accepted manuscript. For information on re-use, please refer to the publisher’s terms and conditions.
UCL classification: UCL
UCL > Provost and Vice Provost Offices > UCL BEAMS
UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences
UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences > Dept of Chemistry
URI: https://discovery-pp.ucl.ac.uk/id/eprint/10167633
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