Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 133, Issue 45, Pages 18183-18193Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja203978r
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Funding
- TSRI
- NIH (NIGMS) [1 R01 GM084019-02]
- Amgen
- Eli Lilly
- A. P. Sloan Foundation
- NSF GRFP
- NDSEG
- Skaggs Oxford Scholarship
- ACS SEED
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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 Ag2CO3 as the oxidant, a fast, high-yielding, operationally simple, and functional group-tolerant protocol has been developed for the cross-coupling of phenyl acetic 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.
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