Seoyoung Kim, Matthew J. Goldfogel, M. M. Gilbert
May 15, 2020
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Journal
Journal of the American Chemical Society
Abstract
Alkyl chlorides and aryl chlorides are among the most abundant and stable carbon electrophiles. Although their coupling with carbon nucleophiles is well developed, the cross-electrophile coupling of aryl chlorides with alkyl chlorides has remained a challenge. We report here the first general approach to this transformation. The key to produc-tive, selective cross-coupling is the use of a small amount of iodide or bromide along with a recently reported ligand, pyridine-2,6-bis(N-cyanocarboxamidine) (PyBCamCN). The scope of the reaction is demonstrated with 35 examples (63% ±16% ave yield) and we show that the Br- and I- ad-ditives act as co-catalysts, generating a low, steady-state concentration of more-reactive alkyl bromide/iodide.