Cooperative Iodide Pd(0)-Catalysed Coupling of Alkoxyallenes and N-Tosylhydrazones: A Selective Synthesis of Conjugated and Skipped Dienes

被引：21

作者：

Parisotto, Stefano ^{[1
]}

Palagi, Lorenzo ^{[1
]}

Prandi, Cristina ^{[1
]}

Deagostino, Annamaria ^{[1
]}

机构：

[1] Univ Torino, Dept Chem, Via Giuria 7, I-10125 Turin, Italy

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2018年 / 24卷 / 21期

关键词：

alkoxyallenes; dienes; iodide; palladium; tosylhydrazones; CATALYZED AUTOTANDEM REACTIONS; BORON-SUBSTITUTED 1,3-DIENES; STEREOSELECTIVE-SYNTHESIS; ASYMMETRIC ADDITION; DIAZO-COMPOUNDS; BOND FORMATION; ALLYL HALIDES; VINYLALUMINUM REAGENTS; VERSATILE REAGENTS; ORGANIC-SYNTHESIS;

D O I：

10.1002/chem.201800765

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Palladium(0)-catalysed hydro-alkylation or -alkenylation of alkoxyallenes with N-tosylhydrazones gives direct access to conjugated and skipped 1-alkoxydienes with high efficiency and excellent functional-group compatibility. The reaction is proposed to involve the insitu-formed t-butanol as proton source in the key step of the allylpalladium(II) species generation. Moreover, lithium iodide or iodobenzene are employed as an unprecedented iodide (I-) reservoir to sustain the catalytic cycle.

引用

页码：5484 / 5488

页数：5

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