Alkyl-(Hetero)Aryl Bond Formation Via Decarboxylative Cross-Coupling: A Systematic Analysis

Overview

Journal Angew Chem Int Ed Engl

Specialty Chemistry

Date 2017 Feb 11

PMID 28185368

Citations 24

Authors

Frederik Sandfort

Matthew J ONeill

Josep Cornella

Laurin Wimmer

Phil S Baran

Affiliations

Soon will be listed here.

Abstract

Suzuki, Negishi, and Kumada couplings are some of the most important reactions for the formation of skeletal C-C linkages. Their widespread use to forge bonds between two aromatic rings has enabled every branch of chemical science. The analogous union between alkyl halides and metallated aryl systems has not been as widely employed due to the lack of commercially available halide building blocks. Redox-active esters have recently emerged as useful surrogates for alkyl halides in cross-coupling chemistry. Such esters are easily accessible through reactions between ubiquitous carboxylic acids and coupling agents widely used in amide bond formation. This article features an amalgamation of in-house experience bolstered by approximately 200 systematically designed experiments to accelerate the selection of ideal reaction conditions and activating agents for the cross-coupling of primary, secondary, and tertiary alkyl carboxylic acids with both aryl and heteroaryl organometallic species.

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