Organic Chemistry

Carboxylating stubborn alkyl chlorides

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Science  08 Jul 2016:
Vol. 353, Issue 6295, pp. 134-135
DOI: 10.1126/science.353.6295.134-d

The utility of alkyl chlorides and carbon dioxide (CO2) as reagents in organic synthesis is often limited by the difficulty of activating these molecules. Börjesson et al. have overcome both these challenges with a nickel catalyst that adds CO2 at ambient pressures to unactivated alkyl chlorides (primary, secondary, and even tertiary). The nickel catalyst ligands that were most effective at minimizing side reactions were 1,10-phenanthrolines with ortho-substituents. The nickel center displaced chloride to create a nucleophile that could then react with electrophilic CO2. The reaction is tolerant of aliphatic alcohol or phenol groups, which helps minimize the need for protecting groups.

J. Am. Chem. Soc. 10.1021/jacs.6b04088 (2016).

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