Nickel-Catalyzed Cross-Electrophile Coupling of Aryl Chlorides with Primary Alkyl Chlorides.

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 productive, 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) (PyBCam^CN). The scope of the reaction is demonstrated with 35 examples (63 ± 16% average yield), and we show that the Br^- and I^- additives act as cocatalysts, generating a low, steady-state concentration of more-reactive alkyl bromide/iodide.

SUBMITTER: Kim S 

PROVIDER: S-EPMC7418462 | biostudies-literature |

REPOSITORIES: biostudies-literature