American Chemical Society
ol2c01942_si_001.pdf (3.54 MB)

Ni/Photoredox-Catalyzed C(sp2)–C(sp3) Cross-Coupling of Alkyl Pinacolboronates and (Hetero)Aryl Bromides

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journal contribution
posted on 2022-08-16, 08:14 authored by Anthony N. Cauley, Antonio Ramirez, Chandan L. Barhate, Andrew F. Donnell, Purnima Khandelwal, Melda Sezen-Edmonds, Trevor C. Sherwood, Jack L. Sloane, Cullen L. Cavallaro, Eric M. Simmons
Utilizing quinoline as a mild, catalytic additive, broadly applicable conditions for the Ni/photoredox-catalyzed C­(sp2)–C­(sp3) cross-coupling of (hetero)­aryl bromides and alkyl pinacolboronate esters were developed, which can be applied to both batch and flow reactions. In addition to primary benzylic nucleophiles, both stabilized and nonstabilized secondary alkyl boronic esters are effective coupling partners. Density functional theory calculations suggest that alkyl radical generation occurs from an alkyl-B­(pin)-quinoline complex, which may proceed via an energy transfer process.