Cobalt-catalyzed Multisubstituted Allylation of the Chelation-assisted C-H Bond of (hetero)arenes with Cyclopropenes

Overview

Journal Chem Sci

Publisher Royal Society of Chemistry

Specialty Chemistry

Date 2021 Nov 15

PMID 34777763

Citations 1

Authors

Kuppan Ramachandran

Pazhamalai Anbarasan

Affiliations

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Abstract

Cyclopropenes are highly strained three-membered carbocycles, which offer unique reactivity in organic synthesis. Herein, Cp*Co-catalyzed ring-opening isomerization of cyclopropenes to cobalt vinylcarbene has been utilized for the synthesis of multisubstituted allylarenes directing group-assisted functionalization of C-H bonds of arenes and heteroarenes. Employing this methodology, various substituents can be introduced at all three carbons of the allyl moiety with high selectivity. The important highlights are excellent functional group tolerance, multisubstituted allylation, high selectivity, gram scale synthesis, removable directing group, and synthesis of cyclopenta[]indoles. In addition, a potential cobaltocycle intermediate was identified and a plausible mechanism is also proposed.

Citing Articles

Ring Transformation of Cyclopropenes to Benzo-Fused Five-Membered Oxa- and Aza-Heterocycles via a Formal [4+1] Cyclization.

Gu F, Lin B, Peng Z, Liu S, Wu Y, Luo M Adv Sci (Weinh). 2024; 11(40):e2407931.

PMID: 39206752 PMC: 11516165. DOI: 10.1002/advs.202407931.

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