Palladium-catalyzed functionalization of indoles with 2-acetoxymethyl-substituted electron-deficient alkenes

被引：63

作者：

Ma, Shengming ^{[1
]}

Yu, Shichao ^{[1
]}

Peng, Zhihua ^{[1
]}

Guo, Hao ^{[1
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organomet Chem, Shanghai 200032, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2006年 / 71卷 / 26期

关键词：

D O I：

10.1021/jo061546s

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

New functionalizations of indoles via palladium-catalyzed reaction of indoles and 2-acetoxymethyl-substituted electron-deficient alkenes are reported. It was found that for N-protected indoles the reaction proceeded smoothly in the presence of 5 mol % of Pd(acac)(2) and 10 mol % of PPh3 at 80 degrees C in HOAc, while for N-unprotected indoles, the reaction was carried out by using 5 mol % of Pd(dba)(2) or 2.5 mol % of Pd-2(dba)(3), CHCl3 with 10 mol % of 2,2'-bipyridine as the catalyst in toluene. This strategy allows the selective installation of electron-deficient olefin functionality at the 3-position of indoles, which might be difficult to obtain by other methods and can be further elaborated.

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页码：9865 / 9868

页数：4

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