Palladium-Catalyzed/Norbornene-Mediated C-H Activation/N-Tosylhydrazone Insertion Reaction: A Route to Highly Functionalized Vinylarenes

被引：47

作者：

Zhou, Ping-Xin ^{[1
]}

Zheng, Lan ^{[1
]}

Ma, Jun-Wei ^{[1
]}

Ye, Yu-Ying ^{[1
]}

Liu, Xue-Yuan ^{[1
]}

Xu, Peng-Fei ^{[1
]}

Liang, Yong-Min ^{[1
,2
]}

机构：

[1] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China

[2] Chinese Acad Sci, Lanzhou Inst Chem Phys, State Key Lab Solid Lubricat, Lanzhou 730000, Peoples R China

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2014年 / 20卷 / 22期

基金：

美国国家科学基金会;

关键词：

CH activation; CC coupling; diazo compounds; palladium; synthetic methods; ALKYLATION-ALKENYLATION REACTIONS; TETRASUBSTITUTED HELICAL ALKENES; SUBSTITUTED ARYL IODIDES; ASYMMETRIC MULTICOMPONENT REACTIONS; NITROGEN-CONTAINING HETEROCYCLES; CROSS-COUPLING REACTIONS; CATALYZED SYNTHESIS; N-TOSYLHYDRAZONES; INTRAMOLECULAR ETA(2)-ARENE; DIAZOCARBONYL COMPOUNDS;

D O I：

10.1002/chem.201402097

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A straightforward method for the synthesis of highly functionalized vinylarenes through palladium-catalyzed, norbornene-mediated CH activation/carbene migratory insertion is described. Extension to a one-pot procedure is also developed. Furthermore, this method can also be used to generate polysubstituted bicyclic molecules. The reaction proceeds under mild conditions to give the products in satisfactory yields using readily available starting materials. This is a Catellani-Lautens reaction that incorporates different types of coupling partners. Additionally, this reaction is the first to demonstrate the possibility of combining Pd-catalyzed insertion of diazo compounds and Pd-catalyzed CH activation.

引用

页码：6745 / 6751

页数：7

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