采用蒽标记钯催化剂的聚合物辅助溶液相（PASP）铃木偶联反应。

Polymer-assisted solution-phase (PASP) Suzuki couplings employing an anthracene-tagged palladium catalyst.

作者信息

Lan Ping, Berta Daniela, Porco John A, South Michael S, Parlow John J

机构信息

Department of Medicinal and Combinatorial Chemistry, Pharmacia Corporation, 800 North Lindbergh Boulevard, St. Louis, Missouri 63167, USA.

出版信息

J Org Chem. 2003 Dec 12;68(25):9678-86. doi: 10.1021/jo035129g.

DOI:10.1021/jo035129g

PMID:14656094

Abstract

A general method for polymer-assisted solution-phase (PASP) Suzuki reactions employing a combination of anthracene-tagged palladium catalyst and anthracene-tagged boronic acid with a polymer-supported carbonate base is reported. The anthracene-tagged catalyst allows for the easy removal of the Pd catalyst along with the dissociated phosphine ligand and phosphine oxide byproducts by sequestration through a chemoselective Diels-Alder reaction with a maleimide resin. The polymer-supported carbonate base facilitates the removal of excess boronic acid and the borane-containing byproducts present at the end of the coupling reaction. The Suzuki coupling reaction can be efficiently conducted by using combinations of the anthracene-tagged Pd catalyst, polymer-supported carbonate base, and anthracene-tagged boronic acid to yield the desired product in high purity and yield without the use of chromatography.

摘要

报道了一种聚合物辅助的溶液相（PASP）铃木反应的通用方法，该方法采用蒽标记的钯催化剂和蒽标记的硼酸与聚合物负载的碳酸盐碱相结合。蒽标记的催化剂能够通过与马来酰亚胺树脂的化学选择性狄尔斯-阿尔德反应螯合，轻松去除钯催化剂以及解离的膦配体和氧化膦副产物。聚合物负载的碳酸盐碱有助于去除过量的硼酸以及偶联反应结束时存在的含硼副产物。通过使用蒽标记的钯催化剂、聚合物负载的碳酸盐碱和蒽标记的硼酸的组合，可以高效地进行铃木偶联反应，从而在不使用色谱法的情况下以高纯度和高产率得到所需产物。