A bimetallic catalyst and dual role catalyst:: Synthesis of N-(alkoxycarbonyl)indoles from 2-(alkynyl)phenylisocyanates

被引：115

作者：

Kamijo, S

Yamamoto, Y ^{[1
]}

机构：

[1] Tohoku Univ, Grad Sch Sci, Res Ctr Sustainable Mat Engn, Inst Multidisciplinary Res Adv Mat, Sendai, Miyagi 9808578, Japan

[2] Tohoku Univ, Grad Sch Sci, Dept Chem, Sendai, Miyagi 9808578, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2003年 / 68卷 / 12期

关键词：

D O I：

10.1021/jo034254p

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

3-Allyl-N-(alkoxycarbonyl)indoles are synthesized via the reaction of 2-(alkynyl)phenylisocyanates and allyl carbonates in the presence of Pd(PPh3)(4) (1 mol %) and CuCl (4 mol %) bimetallic catalyst. It is most probable that Pd-0 acts as a catalyst for the formation of a pi-allylpalladium alkoxide intermediate and Cu-I behaves as a Lewis acid to activate the isocyanate, and the cyclization step proceeds with a cooperative catalytic activity of Pd and Cu. On the other hand, N-(alkoxycarbonyl)indoles are produced via the reaction of 2-(alkynyl)phenylisocyanates and alcohols under a catalytic amount of Na2PdCl4 (5 mol %) or PtCl2 (5 mol %). Pd-II or Pt-II catalyst exhibits dual roles; it acts as a Lewis acid to accelerate the addition of alcohols to isocyanates and as a typical transition-metal catalyst to activate the alkyne for the subsequent cyclization.

引用

页码：4764 / 4771

页数：8

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