The College of Chemistry and Molecular Engineering, Henan Key Laboratory of Chemical Biology and Organic Chemistry, Zhengzhou University, Zhengzhou 450052, People's Republic of China.
J Org Chem. 2013 May 3;78(9):4543-50. doi: 10.1021/jo400574d. Epub 2013 Apr 22.
A highly efficient and practical protocol for palladacycle-catalyzed decarboxylative coupling of alkynyl carboxylic acids with aryl chlorides was developed. The reaction could proceed smoothly in air within 3 h under optimized reaction conditions (1 mol % of palladacycle, 4 mol % of Xphos, 2.0 equiv of K2CO3 in xylene/H2O), affording the corresponding internal alkynes in mostly good to excellent yields. Remarkably, this result represents the first successful examples of this type of decarboxylative cross-coupling using electron-poor, electron-neutral and even inactive sterically hindered electron-rich aryl chlorides as the starting materials.
发展了一种高效实用的钯环催化炔基羧酸与芳基氯脱羧偶联的反应协议。在优化的反应条件下（钯环 1 mol%，Xphos 4 mol%，K2CO3 在二甲苯/H2O 中 2.0 当量），反应可以在空气中 3 小时内顺利进行，主要得到收率良好到优秀的相应的内部炔烃。值得注意的是，这一结果代表了使用缺电子、电中性甚至不活泼的空间位阻富电子芳基氯作为起始原料进行此类脱羧交叉偶联的首例成功实例。
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