卤代咪唑、卤代噁唑和卤代噻唑的双卤化物在催化剂控制下的区域选择性 Suzuki 偶联反应。

Catalyst-controlled regioselective Suzuki couplings at both positions of dihaloimidazoles, dihalooxazoles, and dihalothiazoles.

机构信息

Department of Process Chemistry, Merck Research Laboratories, Merck & Co., Inc., P.O. Box 2000, Rahway, New Jersey 07065, USA.

出版信息

J Org Chem. 2010 Mar 5;75(5):1733-9. doi: 10.1021/jo100148x.

DOI:10.1021/jo100148x

PMID:20141223

Abstract

Various dihaloazoles can be monoarylated at a single C-X bond with high selectivity via Suzuki coupling. By changing the palladium catalyst employed, the selectivity can be switched for some dihaloazoles, allowing for Suzuki coupling at the other, traditionally less reactive C-X bond. These conditions are applicable to coupling of a wide variety of aryl-, heteroaryl-, cyclopropyl-, and vinylboronic acids with high selectivities and enable the rapid construction of diverse arrays of diarylazoles in a modular fashion.

摘要

各种二卤代氮唑可以通过 Suzuki 偶联在单个 C-X 键上高选择性地单芳基化。通过改变所使用的钯催化剂，可以为一些二卤代氮唑切换选择性，从而在另一个传统上反应性较低的 C-X 键上进行 Suzuki 偶联。这些条件适用于各种芳基、杂芳基、环丙基和乙烯基硼酸的偶联，具有高选择性，并能够以模块化的方式快速构建各种二芳基氮唑。