Synthesis of α-haloenamides via zinc halide mediated direct addition of benzhydryl halides to ynamides

被引：10
作者：
Chen, Ling [1 ]
Yu, Lian [1 ]
Deng, Yuan [1 ]
Cui, Yuming [1 ]
Bian, Gaofeng [1 ]
Cao, Jian [1 ]
机构：
[1] Hangzhou Normal Univ, Key Lab Organosilicon Chem & Mat Technol, Minist Educ, Hangzhou, Zhejiang, Peoples R China
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2016年 / 14卷 / 02期
基金：
中国国家自然科学基金;
关键词：
STEREOSELECTIVE-SYNTHESIS; ENAMIDES; CYCLOISOMERIZATION; REGIO; MILD;
D O I：
10.1039/c5ob01950h
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A regio- and stereoselective synthesis of highly substituted alpha-haloenamides was described via the zinc halide mediated direct addition of benzhydryl halides to ynamides under mild conditions. The products alpha-haloenamides were further transformed into multisubstituted enamides via Suzuki and Sonogashira cross-coupling reactions.
引用
收藏
页码：564 / 569
页数：6
相关论文
共 31 条
  • [1] New and Efficient Iron Halide Mediated Synthesis of Alkenyl Halides through Coupling of Alkynes and Alcohols
    Biswas, Srijit
    Maiti, Sukhendu
    Jana, Umasish
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (14) : 2354 - 2359
  • [2] Enamides: valuable organic substrates
    Carbery, David R.
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2008, 6 (19) : 3455 - 3460
  • [3] Regiocontrolled carbometallation reactions of ynamides
    Chechik-Lankin, H
    Livshin, S
    Marek, I
    [J]. SYNLETT, 2005, (13) : 2098 - 2100
  • [4] Divergent Synthesis of 2-Aminofurans via Palladium-Catalyzed Acetoxylative, Alkoxylative, and Hydroxylative Cycloisomerization of Homoallenyl Amides
    Cheng, Cungui
    Liu, Shuiyou
    Zhu, Gangguo
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (15) : 7604 - 7612
  • [5] Palladium-Catalyzed Cycloisomerization and Aerobic Oxidative Cycloisomerization of Homoallenyl Amides: A Facile and Divergent Approach to 2-Aminofurans
    Cheng, Cungui
    Liu, Shuiyou
    Zhu, Gangguo
    [J]. ORGANIC LETTERS, 2015, 17 (06) : 1581 - 1584
  • [6] Stereoselective hydrofluorination of ynamides: a straightforward synthesis of novel α-fluoroenamides
    Compain, Guillaume
    Jouvin, Kevin
    Martin-Mingot, Agnes
    Evano, Gwilherm
    Marrot, Jerome
    Thibaudeau, Sebastien
    [J]. CHEMICAL COMMUNICATIONS, 2012, 48 (42) : 5196 - 5198
  • [7] Ynamides: A Modern Functional Group for the New Millennium
    DeKorver, Kyle A.
    Li, Hongyan
    Lohse, Andrew G.
    Hayashi, Ryuji
    Lu, Zhenjie
    Zhang, Yu
    Hsung, Richard P.
    [J]. CHEMICAL REVIEWS, 2010, 110 (09) : 5064 - 5106
  • [8] Evano G., 2013, SYNTHESIS-STUTTGART, P17
  • [9] Ynamides: Versatile Tools in Organic Synthesis
    Evano, Gwilherm
    Coste, Alexis
    Jouvin, Kevin
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (16) : 2840 - 2859
  • [10] Controlled Synthesis of 1,3,5-Oxadiazin-2-ones and Oxazolones through Regioselective lodocyclization of Ynamides
    Huang, Hai
    Zhu, Xiaolin
    He, Guangke
    Liu, Qi
    Fan, Junzhen
    Zhu, Hongjun
    [J]. ORGANIC LETTERS, 2015, 17 (10) : 2510 - 2513
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