Decarboxylative Suzuki-Miyaura coupling of (hetero)aromatic carboxylic acids using iodine as the terminal oxidant

被引:22
作者
Quibell, Jacob M. [1 ]
Duan, Guojian [1 ,2 ]
Perry, Gregory J. P. [1 ]
Larrosa, Igor [1 ]
机构
[1] Univ Manchester, Sch Chem, Oxford Rd, Manchester M13 9PL, Lancs, England
[2] Gansu Univ Chinese Med, Coll Pharm, Lanzhou 730000, Gansu, Peoples R China
基金
中国国家自然科学基金;
关键词
C-H BORYLATION; CATALYZED BORYLATION; ARYL CHLORIDES; ASYMMETRIC HYDROBORATION; AROMATIC CARBOXYLATES; BIARYL SYNTHESIS; METAL-CATALYSTS; ARYLATION; FUNCTIONALIZATION; ORGANOBORANES;
D O I
10.1039/c9cc01817d
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A novel methodology for the decarboxylative Suzuki-Miyaura-type coupling has been established. This process uses iodine or a bromine source as both the decarboxylation mediator and the terminal oxidant, thus avoiding the need for stoichiometric amounts of transition metal salts previously required. Our new protocol allows for the construction of valuable biaryl architectures through the coupling of (hetero)aromatic carboxylic acids with arylboronic acids. The scope of this decarboxylative Suzuki reaction has been greatly diversified, allowing for previously inaccessible non-ortho-substituted aromatic acids to undergo this transformation. The procedure also benefits from low catalyst loadings and the absence of stoichiometric transition metal additives.
引用
收藏
页码:6445 / 6448
页数:4
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