Palladium-Catalyzed Aryl Iodide Carbonylation as a Route to Imidazoline Synthesis: Design of a Five-Component Coupling Reaction

被引：39
|
作者：
Bontemps, Sebastien [1 ,2 ]
Quesnel, Jeffrey S. [1 ,2 ]
Worrall, Kraig [1 ,2 ]
Arndtsen, Bruce A. [1 ,2 ]
机构：
[1] McGill Univ, Dept Chem, Montreal, PQ H3A 2K6, Canada
[2] Univ Toulouse, UPS, INPT, F-31077 Toulouse, France
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2011年 / 50卷 / 38期
基金：
加拿大自然科学与工程研究理事会;
关键词：
carbonylation; cyclizations; heterocycles; multicomponent reactions; palladium; AMINO-ACID DERIVATIVES; AMIDE BOND FORMATION; MULTICOMPONENT SYNTHESIS; CARBON-MONOXIDE; ENANTIOPURE IMIDAZOLINES; ATMOSPHERIC-PRESSURE; N-SULFONYLIMINES; VINYLIC HALIDES; BETA-LACTAMS; 2-IMIDAZOLINES;
D O I：
10.1002/anie.201103885
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Take five: A new method employing aryl halide carbonylation to directly access heterocycles has been described (see scheme). In a single palladium-catalyzed reaction the catalyst mediates two consecutive carbonylation steps, thereby converting five components (aryl iodide, two units imine, and two units CO) into an imidazoline ring. © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码：8948 / 8951
页数：4
相关论文
共 50 条
  • [31] Cascade synthesis of quinazolinones from 2-aminobenzonitriles and aryl bromides via palladium-catalyzed carbonylation reaction
    Li, Haoquan
    He, Lin
    Neumann, Helfried
    Beller, Matthias
    Wu, Xiao-Feng
    GREEN CHEMISTRY, 2014, 16 (03) : 1336 - 1343
  • [32] A general synthesis of a-aryl and heteroarylpyrroles by palladium-catalyzed coupling reaction of a-tributylstannylpyrrole with aryl and heteroaryl halides
    Wang, J.
    Scott, A. I.
    Tetrahedron Letters, 37 (19):
  • [33] Palladium-catalyzed cross-coupling reaction of aryl(trialkyl)silanes with aryl nitriles
    Tang, Shi
    Li, Shu-Hua
    Yan, Wen-bin
    TETRAHEDRON LETTERS, 2012, 53 (50) : 6743 - 6746
  • [34] SYNTHESIS OF 5-ARYL AND VINYL TETRAZOLES BY THE PALLADIUM-CATALYZED CROSS-COUPLING REACTION
    YI, KY
    YOO, SE
    TETRAHEDRON LETTERS, 1995, 36 (10) : 1679 - 1682
  • [35] A GENERAL SYNTHETIC METHOD FOR ORSELLINIC ACID MOIETY OF MACROLIDES BY THE PALLADIUM-CATALYZED CARBONYLATION OF ARYL IODIDE AND ITS APPLICATION TO ZEARALENONE SYNTHESIS
    TAKAHASHI, T
    NAGASHIMA, T
    TSUJI, J
    CHEMISTRY LETTERS, 1980, (04) : 369 - 372
  • [36] Novel route for the synthesis of allylboronates: Palladium-catalyzed three-component coupling reaction of allenes, organic halides, and diborons.
    Yang, FY
    Cheng, CH
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2000, 219 : U196 - U196
  • [37] PALLADIUM-CATALYZED REACTION OF VINYLMAGNESIUM BROMIDE AND ARYL IODIDES AS A CONVENIENT ROUTE TO STYRENES
    BUMAGIN, NA
    ANDRIUKHOVA, NP
    BELETSKAIA, IP
    DOKLADY AKADEMII NAUK SSSR, 1987, 297 (05): : 1126 - 1129
  • [38] Palladium-Catalyzed Carbonylation of Indoles for Synthesis of Indol-3-yl Aryl Ketones
    Zhao, Mi-Na
    Ran, Longfei
    Chen, Ming
    Ren, Zhi-Hui
    Wang, Yao-Yu
    Guan, Zheng-Hui
    ACS CATALYSIS, 2015, 5 (02): : 1210 - 1213
  • [39] Palladium-Catalyzed Three-Component Cascade Carbonylation Reaction to Construct Benzofuran Derivatives
    Li, Ming
    Xu, Shanmei
    Chen, Dong-Ping
    Gao, Fan
    Li, Shun-Xi
    Zhu, Shuang-Xi
    Qiu, Yi-Feng
    Quan, Zheng-Jun
    Wang, Xi-Cun
    Liang, Yong-Min
    JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (11): : 7741 - 7746
  • [40] PALLADIUM-CATALYZED CARBONYLATION OF VINYL HALIDES - A ROUTE TO THE SYNTHESIS OF ALPHA-METHYLENE LACTONES
    MARTIN, LD
    STILLE, JK
    JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (19): : 3630 - 3633
12345