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

被引:138
作者
Engle, Keary M. [1 ]
Thuy-Boun, Peter S. [1 ]
Dang, Michael [1 ]
Yu, Jin-Quan [1 ]
机构
[1] Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
关键词
C-H ACTIVATION; CATALYZED DIRECT ARYLATION; PD-II-HYDRIDE; REDUCTIVE-ELIMINATION PATHWAY; CARBON-HYDROGEN BONDS; MOLECULAR-OXYGEN; PALLADIUM COMPLEXES; BORONIC ACIDS; BENZOIC-ACIDS; HETEROAROMATIC-COMPOUNDS;
D O I
10.1021/ja203978r
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
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.
引用
收藏
页码:18183 / 18193
页数:11
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