Synthesis of Benzylureas and Related Amine Derivatives Via Copper-Catalyzed Three-Component Carboamination of Styrenes

Overview

Journal Org Lett

Publisher American Chemical Society

Specialties Biochemistry
Chemistry

Date 2020 Oct 19

PMID 33074005

Citations 7

Authors

Jonathan J Kennedy-Ellis

Erik D Boldt

Sherry R Chemler

Affiliations

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Abstract

A direct assembly of secondary benzylureas and related amine derivatives via copper-catalyzed carboamination of styrenes with potassium alkyltrifluoroborates and ureas, anilines, or an amide is reported. Terminal and 1,2-disubstituted alkenes, as well as dienes, participate in this three-component coupling reaction. The reaction mechanism likely involves the addition of an alkyl radical to the styrene, followed by metal-mediated oxidative coupling of the resulting benzylic radical with the amine derivative. Factors that impact substrate reactivity and regioselectivity are discussed.

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