Rhodium-Catalyzed (4+1) Cycloaddition Between Benzocyclobutenones and Styrene-Type Alkenes

Overview

Journal Angew Chem Int Ed Engl

Specialty Chemistry

Date 2022 Mar 15

PMID 35289979

Authors

Shusuke Ochi

Zining Zhang

Ying Xia

Guangbin Dong

Affiliations

Soon will be listed here.

Abstract

Herein, we describe a unique one-carbon ring-expansion strategy to access multi-substituted 2-indanones from benzocyclobutenones and styrene-type olefins. The use of a cationic "ligandless" rhodium catalyst was the key for both high reactivity and selectivity towards the (4+1) product. Broad functional group tolerance, a good substrate scope, and scalability have been demonstrated. Computation studies reveal that the origin of the (4+1) selectivity is due to a facile β-H elimination pathway that reduces the overall barrier of the turnover-limiting C-C reductive elimination step.

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