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

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-...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2011-11, Vol.133 (45), p.18183-18193
Main Authors: Engle, Keary M, Thuy-Boun, Peter S, Dang, Michael, Yu, Jin-Quan
Format: Article
Language:English
Subjects:
Borates - chemistry
Catalysis
Ligands
Molecular Structure
Organometallic Compounds - chemistry
Palladium - chemistry
Phenylacetates - chemical synthesis
Phenylacetates - chemistry
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Summary: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.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja203978r