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Ligand-accelerated cross-coupling of C(sp2)-H bonds with arylboron reagents.

ABSTRACT: A ligand-accelerated Pd(II)-catalyzed C(sp(2))-H/arylboron cross-coupling reaction of phenylacetic acid substrates is reported. Using Ac-Ile-OH as the ligand and Ag(2)CO(3) 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 O(2) as the sole reoxidant, which sheds light on the path forward in developing optimized ligands for aerobic C-H/arylboron cross-coupling.

SUBMITTER: Engle KM

PROVIDER: S-EPMC3230269 | biostudies-literature | 2011 Nov

REPOSITORIES: biostudies-literature

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Ligand-accelerated cross-coupling of C(sp2)-H bonds with arylboron reagents.

Engle Keary M KM Thuy-Boun Peter S PS Dang Michael M Yu Jin-Quan JQ

Journal of the American Chemical Society 20111021 45

A ligand-accelerated Pd(II)-catalyzed C(sp(2))-H/arylboron cross-coupling reaction of phenylacetic acid substrates is reported. Using Ac-Ile-OH as the ligand and Ag(2)CO(3) 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 O(2) as the sole reoxidant, which sheds light on the ...[more]

PMID: 21913636

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