Pd-catalyzed coupling of β-hydroxy α-diazocarbonyl compounds with aryl iodides: a migratory insertion/β-hydroxy elimination sequence

被引：26
|
作者：
Zhou, Lei
Liu, Yizhou
Zhang, Yan
Wang, Jianbo [1 ]
机构：
[1] Peking Univ, Coll Chem, BNLMS, Beijing 100871, Peoples R China
来源：
CHEMICAL COMMUNICATIONS | 2011年 / 47卷 / 12期
基金：
中国国家自然科学基金; 中国博士后科学基金;
关键词：
RING EXPANSION REACTIONS; STEREOSELECTIVE-SYNTHESIS; CARBENE INSERTION; TETRASUBSTITUTED OLEFINS; C-C; VINYL HALIDES; PALLADIUM; ALLENYLCYCLOBUTANOLS; LITHIODIAZOACETATE; DIAZOESTERS;
D O I：
10.1039/c0cc05523a
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The coupling of beta-hydroxy alpha-diazocarbonyl compounds with aryl halides is described, which proceeds through a Pd-catalyzed migratory insertion/beta-OH elimination sequence. This reaction provides a new route to the synthesis of tetrasubstituted olefins.
引用
收藏
页码：3622 / 3624
页数：3
相关论文
共 50 条
  • [31] Electron-Catalyzed Cross-Coupling of Arylboron Compounds with Aryl Iodides
    Okura, Keisho
    Teranishi, Tsuyoshi
    Yoshida, Yuto
    Shirakawa, Eiji
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (24) : 7186 - 7190
  • [32] Pd-catalyzed carbonyl insertion coupling reactions of a hypervalent iodoheterocycle with alcohols and amines
    Luo, SJ
    Ma, YX
    Liang, YM
    MOLECULES, 2005, 10 (01) : 238 - 243
  • [33] An efficient system for the Pd-catalyzed cross-coupling of amides and aryl chlorides
    Fors, Brett P.
    Dooleweerdt, Karin
    Zeng, Qingle
    Buchwald, Stephen L.
    TETRAHEDRON, 2009, 65 (33) : 6576 - 6583
  • [34] Pd-Catalyzed Decarboxylative Negishi Coupling of Zinc Aryl Carboxylates with Arylthianthrenium Salts
    Zhang, Chun
    Cui, Yangbo
    Zhou, Xiaoyu
    Pan, Yichen
    Zhang, Junqi
    Hu, Dandan
    Guo, Hai-Ming
    Hao, Er-Jun
    Ren, Hongjun
    ORGANIC LETTERS, 2025, 27 (09) : 2256 - 2261
  • [35] Preparation of Unsymmetrical Biaryls by Pd(II)-Catalyzed Cross-Coupling of Aryl Iodides
    Wang, Liqiang
    Lu, Wenjun
    ORGANIC LETTERS, 2009, 11 (05) : 1079 - 1082
  • [36] Synthesis of Arylethylene or Diarylethylene Compounds by Pd-Catalyzed Heck Coupling Reaction
    Yan, Hong
    Sun, Peng
    Qu, Xiaoming
    Lu, Linhua
    Zhu, Yan
    Yang, Hailong
    Mao, Jincheng
    SYNTHETIC COMMUNICATIONS, 2013, 43 (20) : 2773 - 2783
  • [37] A Single-Step Synthesis of Enynes: Pd-Catalyzed Arylalkynylation of Aryl Iodides, Internal Alkynes, and Alkynylsilanes
    Sakai, Norio
    Komatsu, Ryosuke
    Uchida, Naoki
    Ikeda, Reiko
    Konakahara, Takeo
    ORGANIC LETTERS, 2010, 12 (06) : 1300 - 1303
  • [38] Biaryl and Aryl Ketone Synthesis via Pd-Catalyzed Decarboxylative Coupling of Carboxylate Salts with Aryl Triflates
    Goossen, Lukas J.
    Linder, Christophe
    Rodriguez, Nuria
    Lange, Paul P.
    CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (37) : 9336 - 9349
  • [39] Pd-Catalyzed Coupling of γ-C(sp3)-H Bonds of Oxalyl Amide-Protected Amino Acids with Heteroaryl and Aryl Iodides
    Han, Jian
    Zheng, Yongxiang
    Wang, Chao
    Zhu, Yan
    Huang, Zhi-Bin
    Shi, Da-Qing
    Zeng, Runsheng
    Zhao, Yingsheng
    JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (13): : 5681 - 5689
  • [40] A General Pd-Catalyzed Decarboxylative Cross-Coupling Reaction between Aryl Carboxylic Acids: Synthesis of Biaryl Compounds
    Hu, Peng
    Shang, Yaping
    Su, Weiping
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (24) : 5945 - 5949
12345