The first general palladium catalyst for the Suzuki-Miyaura and carbonyl enolate coupling of aryl arenesulfonates

The first general palladium catalyst for the Suzuki-Miyaura and carbonyl enolate coupling of aryl arenesulfonates
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DOI:
10.1021/ja036947t
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发表时间:
2003-10-01
影响因子:
15
通讯作者:
Buchwald, SL
Buchwald, SL
中科院分区:
化学1区
文献类型:
--
作者:
Nguyen, HN;Huang, XH;Buchwald, SL

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第一种钯催化的Suzuki−Miyaura和未活化的芳基芳烃磺酸酯的羰基烯醇化物偶联的通用方法是利用XPhos,1和Pd(OAc)2开发的。这是非常令人感兴趣的,因为甲苯磺酸芳基酯和苯磺酸芳基酯比三氟甲磺酸芳基酯更容易处理并且相当便宜。该催化剂体系在温和条件下实现各种芳基、杂芳基和极受阻芳基硼酸与不同的芳基甲苯磺酸酯的偶联。相同的催化剂用于芳基芳磺酸酯的第一羰基烯醇化物偶联。
The first general method for the palladium-catalyzed Suzuki−Miyaura and carbonyl enolate coupling of unactivated aryl arenesulfonates was developed utilizing XPhos,1, and Pd(OAc)2. This is of significant interest because aryl tosylates and aryl benzenesulfonates are more easily handled and considerably less expensive than aryl triflates. This catalyst system effects the coupling of a variety of aryl, heteroaryl, and extremely hindered arylboronic acids with different aryl tosylates, under mild conditions. The same catalyst was employed in the first carbonyl enolate coupling of aryl arensulfonates.