A highly efficient and simple route for the synthesis of 2-alknyl benzo[]thiazoles has been developed by palladium and copper catalyzed the cross-coupling reaction of 2-thiobenzo[]thiazoles with (hetero)aromatic and aliphatic alkynylaluminum reagents. Various 2-alkynyl benzo[]thiazole derivatives can be obtained in 19–97 % isolated yields using 1 mol% PdCl(dppf)/5 mol% xanthpos as the catalyst and CuI (3 equiv.) as desulfurization agent. The cross-coupling reaction can be carried out smoothly with electron-donating or -withdrawing groups on the aromatic ring of the organo aluminum reagents or the 2-thiobenzo[]thiazoles. Furthermore, the broad substrate scope and the maintenance of high efficiency on a gram scale make this protocol a potentially practical method to synthesize 2-alkynylbenzo[]thiazole derivatives. On the basis of the experimental results, a possible catalytic cycle has been proposed.2009 Elsevier Ltd. All rights reserved.

中文翻译：

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铜辅助钯催化烷基丙烷试剂与2-硫代苯并[d]噻唑通过C-S键断裂发生交叉偶联反应

通过钯和铜催化2-硫代苯并[]噻唑与(杂)芳香族和脂肪族炔基铝试剂的交叉偶联反应，开发了一种高效、简单的合成2-炔基苯并[]噻唑的路线。使用 1 mol% PdCl(dppf)/5 mol% xantpos 作为催化剂和 CuI（3 当量）作为脱硫剂，可以以 19-97% 的分离收率获得各种 2-炔基苯并[]噻唑衍生物。有机铝试剂或2-硫代苯并[]噻唑类化合物芳香环上的给电子或吸电子基团可以顺利地进行交叉偶联反应。此外，广泛的底物范围和克级高效率的维持使该方案成为合成 2-炔基苯并[]噻唑衍生物的潜在实用方法。根据实验结果，提出了一种可能的催化循环。2009 Elsevier Ltd. 保留所有权利。