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Site-selective bromination of sp3 C–H bonds Chem.Sci Sathyamoorthi, S., Banerjee, S., Du Bois, J., Burns, N. Z., Zare, R. N. 2018; 9: 100-104

Abstract

A method for converting sp3 C-H to C-Br bonds using an N-methyl sulfamate directing group is described. The reaction employs Rh2(oct)4 and a mixture of NaBr and NaOCl and is performed in aqueous solution open to air. For all sulfamates examined, oxidation occurs with high selectivity at the ?-carbon, affording a uniquely predictable method for C-H bond halogenation. Results from a series of mechanistic experiments suggest that substrate oxidation likely proceeds by a radical chain process. Initial formation of an N-halogenated sulfamate followed by Rh-mediated homolysis generates an N-centered radical, which serves as the active oxidant.

View details for DOI 10.1039/C7SC04611A

View details for PubMedCentralID PMC5873043