Free Radical Pathway Cleavage of C-O Bonds for the Synthesis of Alkylboron Compounds

.Summary of main observation and conclusion We report a silver-catalyzed borylation of alkyl tosylates, which provides a new method for the synthesis of alkylboron compounds with good functional group compatibility and excellent chemoselectivity. The present work added highly polarized alkyl tosylate C-O bonds to the fairly limited number of C-O bonds able to participate in free radical cleavage pathways. The mechanistic studies suggested that in situ-generated silver(0) catalytic species were the active catalytic species and played a key role in the radical pathway cleavage of C-O bonds.