Electrophilic Activation of Benzaldehydes through ortho Palladation: One-Pot Synthesis of 3-Methylene-indan-1-ols through a Domino Allylstannylation/Heck Reaction under Neutral Conditions

被引：27

作者：

Cvengros, Jan ^{[1
]}

Schuette, Jutta ^{[1
]}

Schloerer, Nils ^{[1
]}

Neudoerfl, Joerg ^{[1
]}

Schmalz, Hans-Guenther ^{[1
]}

机构：

[1] Univ Cologne, Dept Chem, D-50939 Cologne, Germany

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2009年 / 48卷 / 33期

关键词：

allylation; domino reactions; Heck reaction palladium; stannanes; HECK REACTION; PALLADIUM; ALLYLATION; COMPLEXES; PESTALONE; ALDEHYDES; CATALYSTS; HALIDES;

D O I：

10.1002/anie.200901837

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Active neighbors: The Pd-catalyzed reaction of orthoiodo- and ortho-trifluoromethanesulfonyloxy(OTf) benzaldehydes with allyltributylstannane gives 3- alkylidene-1-indanols (see scheme). The allylation/Heck reaction involves a new catalytic activation mode: the electrophilic activation of an aldehyde group by a Lewis acidic PdII center generated at the ortho position by oxidative addition. Alkoxystannanes serve as a base equivalent, allowing Heck-type transformations under neutral conditions. © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：6148 / 6151

页数：4

共 37 条

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