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Ligand-Accelerated Cross-Coupling of C(sp2)–H Bonds with Arylboron Reagents

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journal contribution
posted on 22.02.2016, 15:07 by Keary M. Engle, Peter S. Thuy-Boun, Michael Dang, Jin-Quan Yu
A ligand-accelerated Pd(II)-catalyzed C(sp2)–H/arylboron cross-coupling reaction of phenylacetic acid substrates is reported. Using Ac-Ile-OH as the ligand and Ag2CO3 as the oxidant, a fast, high-yielding, operationally simple, and functional group-tolerant protocol has been developed for the cross-coupling of phenylacetic acid substrates with aryltrifluoroborates. This ligand scaffold has also been shown to improve catalysis using 1 atm O2 as the sole reoxidant, which sheds light on the path forward in developing optimized ligands for aerobic C–H/arylboron cross-coupling.

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