Work

Synthesis of α-Substituted β,γ-Unsaturated Cyclobutanecarboxamides via Palladium-Catalyzed Aminocarbonylation of Vinylcyclobutanols

Year: 2025

Type: article

Abstract: Vinylcyclobutanols are highly strained molecules that are prone to semipinacol rearrangement or ring-opening under catalytic conditions, challenging the synthesis of functionalized cyclobutane scaffolds. We report here a palladium-catalyzed aminocarbonylation of vinylcyclobutanols with amine hydrochlorides and CO. The reaction proceeds via in situ formation of conjugated dienes and π-allyl palladium intermediates, furnishing α-substituted β,γ-unsaturated cyclobutanecarboxamides. This method shows a broad substrate scope and excellent functional group tolerance while effectively suppressing rearrangement and ring-opening. It provides a concise, robust route to structurally diverse α-substituted β,γ-unsaturated cyclobutane derivatives bearing a quaternary carbon center.

Source: Organic Letters

DOI: 10.1021/acs.orglett.5c03781

Authors: Yu-Kun Liu, Xiao-Feng Wu

Institutions: Leibniz Institute for Catalysis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian National Laboratory for Clean Energy

Language: English

Topic: Catalytic Cross-Coupling Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $4,500

Funders: China Scholarship Council, Leibniz-Gemeinschaft, National Key Research and Development Program of China