Palladium-Catalyzed Oxidative Cross-Coupling of N-Tosylhydrazones or Diazoesters with Terminal Alkynes: A Route to Conjugated Enynes

被引：144
|
作者：
Zhou, Lei [1 ,2 ]
Ye, Fei [1 ,2 ]
Ma, Jiachen [1 ,2 ]
Zhang, Yan [1 ,2 ]
Wang, Jianbo [1 ,2 ]
机构：
[1] Peking Univ, BNLMS, Beijing 100871, Peoples R China
[2] Peking Univ, Key Lab Bioorgan Chem & Mol Engn, Minist Educ, Coll Chem, Beijing 100871, Peoples R China
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2011年 / 50卷 / 15期
基金：
中国博士后科学基金;
关键词：
alkynes; cross-coupling; enynes; migratory insertion; palladium; ALPHA-DIAZOCARBONYL COMPOUNDS; TO-HEAD DIMERIZATION; CARBENE INSERTION; STEREOSELECTIVE-SYNTHESIS; SELECTIVE DIMERIZATION; MIGRATORY INSERTION; EFFICIENT SYNTHESIS; ARYLBORONIC ACIDS; BENZYL BROMIDES; VINYL HALIDES;
D O I：
10.1002/anie.201007224
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Coming at them from another angle: In a fresh approach to the synthesis of conjugated alkynes, the palladium-catalyzed cross-coupling of N-tosylhydrazones or diazoesters with terminal alkynes provided the desired enyne products with excellent stereoselectivity (see scheme; Ts=p-toluenesulfonyl). The reaction is proposed to involve an unprecedented alkynyl migratory insertion of a palladium carbene complex. Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码：3510 / 3514
页数：5
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