Copper-Catalyzed Regio- and Stereoselective Intermolecular Three-Component Oxyarylation of Allenes

被引：37
|
作者：
Itoh, Taisuke [1 ]
Shimizu, Yohei [1 ]
Kanai, Motomu [1 ,2 ]
机构：
[1] Univ Tokyo, Grad Sch Pharmaceut Sci, Bunkyo Ku, Tokyo 1130033, Japan
[2] Japan Sci & Technol Agcy, ERATO, Kanai Life Sci Catalysis Project, Bunkyo Ku, Tokyo 1130033, Japan
来源：
ORGANIC LETTERS | 2014年 / 16卷 / 10期
关键词：
ELECTROPHILIC CARBOFUNCTIONALIZATION; ALKENE CARBOETHERIFICATION; ALCOHOLS; CARBONYL; HALIDES; ALKYNES; OXYGENATION; OXIDATION; ALDEHYDES; SALTS;
D O I：
10.1021/ol501022d
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A copper(II)-catalyzed intermolecular three-component oxyarylation of allenes using arylboronic acids as a carbon source and TEMPO as an oxygen source is described. The reaction proceeded under mild conditions with high regio- and stereo-selectivity and functional group tolerance. A plausible reaction mechanism is proposed, involving carbocupration of allenes, homolysis of the intervening allylcopper(II), and a radical TEMPO trap.
引用
收藏
页码：2736 / 2739
页数：4
相关论文
共 50 条
  • [31] Copper-Catalyzed Three Component Regio- and Stereospecific Selenosulfonation of Alkynes: Synthesis of (E)-β-Selenovinyl Sulfones
    Liu, Yang
    Zheng, Guangfan
    Zhang, Qian
    Li, Yan
    JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (04): : 2269 - 2275
  • [32] Enantioselective Generation of Adjacent Stereocenters in a Copper-Catalyzed Three-Component Coupling of Imines, Allenes, and Diboranes
    Yeung, Kay
    Ruscoe, Rebecca E.
    Rae, James
    Pulis, Alexander P.
    Procter, David J.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (39) : 11912 - 11916
  • [33] Copper-Catalyzed Three-Component Carboboronation of Allenes Using Highly Strained Cyclic Ketimines as Electrophiles
    Deng, Hao
    Dong, Yujie
    Shangguan, Yu
    Yang, Fazhou
    Han, Sheng
    Wu, Jiaqi
    Liang, Bo
    Guo, Hongchao
    Zhang, Cheng
    ORGANIC LETTERS, 2021, 23 (11) : 4431 - 4435
  • [34] Copper-Catalyzed Regio- and Stereoselective Oxidative Vinylsulfonylation of Quinoxalinones with Alkynes and Sulfonyl Hydrazides
    Clinton, Chayan Dhar
    Prasad, Ch. Durga
    Thombal, Raju S.
    Lee, Yong Rok
    ADVANCED SYNTHESIS & CATALYSIS, 2021, 363 (03) : 776 - 784
  • [35] Efficient stereoselective synthesis of benzoxazines via copper-catalyzed three-component coupling reactions
    Xu, Xiaobing
    Liang, Linfeng
    Liu, Jun
    Yang, Jingyu
    Mai, Lugen
    Li, Yanzhong
    TETRAHEDRON LETTERS, 2009, 50 (01) : 57 - 59
  • [36] Regio- and Diastereoselective Copper-Catalyzed Carbometalation of Cyclopropenylsilanes
    Cohen, Yair
    Marek, Ilan
    ORGANIC LETTERS, 2019, 21 (22) : 9162 - 9165
  • [37] Nickel-catalyzed regio- and diastereoselective intermolecular three-component coupling of oxabicyclic alkenes with alkynes and organoboronic acids
    Mannathan, Subramaniyan
    Cheng, Chien-Hong
    CHEMICAL COMMUNICATIONS, 2013, 49 (15) : 1557 - 1559
  • [38] Copper-catalyzed regio- and stereo-selective hydrosilylation of terminal allenes to access (E)-allylsilanes
    Shaowei Chen
    Xiaoqian He
    Yi Jin
    Yu Lan
    Xiao Shen
    Nature Communications, 13
  • [39] Nickel-Catalyzed Highly Chemo-, Regio-, and Stereoselective Three-Component Reaction of Norbornene with Two Alkynes
    Ogata, Kenichi
    Sugasawa, Jun
    Atsuumi, Yuka
    Fukuzawa, Shin-ichi
    ORGANIC LETTERS, 2010, 12 (01) : 148 - 151
  • [40] Copper-catalyzed, Three-component Polymerization for the Synthesis of Polyphosphonylamidines
    Wang, Wei-hu
    He, Jun-nan
    Zheng, Yu-bin
    Zheng, Nan
    ACTA POLYMERICA SINICA, 2021, 52 (09): : 1129 - 1137
12345