A general and long-lived catalyst for the palladium-catalyzed coupling of aryl halides with thiols

A general and long-lived catalyst for the palladium-catalyzed coupling of aryl halides with thiols
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DOI:
10.1021/ja0580340
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发表时间:
2006-02-22
影响因子:
15
通讯作者:
Hartwig, JF
Hartwig, JF
中科院分区:
化学1区
文献类型:
--
作者:
Fernández-Rodríguez, MA;Shen, QL;Hartwig, JF

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报道了一种基于CyPF-t-Bu配体(1)的芳基卤化物和磺酸盐与硫醇偶联的通用催化体系。1的络合物催化的反应产率高、范围广、转化率高、官能团耐受性高。成交量通常比以前的催化剂高出2到3个数量级。此外,首次报道了芳基对甲苯磺酸盐与烷基硫醇反应生成芳基硫化物的反应。最后,使用硫化氢替代物从两个溴代芳烃合成了二芳硫醚。
A general catalytic system for the coupling of aryl halides and sulfonates with thiols based on the use of the CyPF-t-Bu ligand (1) is reported. The reactions catalyzed by complexes of1occur in excellent yields with broad scope and exhibit extraordinary turnover numbers and high tolerance of functional groups. Turnover numbers usually exceed those of previous catalysts by 2 or 3 orders of magnitude. In addition, the reactions of aryl tosylates with alkane thiols to form aryl sulfides are reported for the first time. Finally, the synthesis of a diarylsulfide from two bromoarenes was accomplished using a hydrogen sulfide surrogate.