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钯催化的多氟代苯甲酸钾与芳基溴化物、氯化物和三氟甲磺酸酯的脱羧交叉偶联。

Pd-catalyzed decarboxylative cross coupling of potassium polyfluorobenzoates with aryl bromides, chlorides, and triflates.

机构信息

Key Laboratory of Bioorganic Phosphorus Chemistry & Chemical Biology (Ministry of Education), Department of Chemistry, Tsinghua University, Beijing, China.

出版信息

Org Lett. 2010 Mar 5;12(5):1000-3. doi: 10.1021/ol100008q.

Abstract

Pd-catalyzed decarboxylative cross coupling of potassium polyfluorobenzoates with aryl bromides, chlorides, and triflates is achieved by using diglyme as the solvent. The reaction is useful for synthesis of polyfluorobiaryls from readily accessible and nonvolatile polyfluorobenzoate salts. Unlike the Cu-catalyzed decarboxylation cross coupling where oxidative addition is the rate-limiting step, in the Pd-catalyzed version decarboxylation is the rate-limiting step.

摘要

使用二甘醇作为溶剂,实现了钯催化的聚氟代苯甲酸钾与芳基溴化物、氯化物和三氟甲磺酸酯的脱羧交叉偶联。该反应可用于从易得且非挥发性的聚氟代苯甲酸盐合成多氟联芳烃。与 Cu 催化的脱羧交叉偶联中氧化加成是速率限制步骤不同,在 Pd 催化的版本中脱羧是速率限制步骤。

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