Rh-catalyzed alkoxycarbonylation of unactivated alkyl chlorides† † Electronic supplementary information (ESI) available. See DOI: https://doi.org/10.1039/d2sc04103k

ABSTRACT: A general rhodium-catalyzed selective carbonylative coupling of unactivated alkyl chlorides with aliphatic alcohols or phenols to the corresponding esters is presented for the first time. Crucial for this transformation is the addition of sodium iodide, which provides in situ more active alkyl iodides. In the presence of a Rh(i)-DPPP catalyst system diverse esters (81 examples) including industrially relevant acetates from chloro- and dichloromethane can be prepared in a straightforward manner in up to 95% isolated yield. The used ligand not only affects the selectivity of the carbonylation reaction but also controls the selectivity of the preceding halide exchange step. An efficient and convenient rhodium-catalyzed alkoxycarbonylation of unactivated alkyl chlorides was developed for the first time. More than 80 examples of esters were prepared directly from readily available substrates with often high selectivity.

SUBMITTER: Wang P 

PROVIDER: S-EPMC9682885 | biostudies-literature | 2022 Nov

REPOSITORIES: biostudies-literature