Efficient synthesis of alkyl aryl ketones & ketals via palladium-catalyzed regioselective arylation of vinyl ethers

被引：32
|
作者：
Liu, Mingcui [1 ]
Hyder, Zeynab [2 ]
Sun, Yawei [1 ]
Tang, Weijun [1 ]
Xu, Lijin [1 ]
Xiao, Jianliang [2 ]
机构：
[1] Renmin Univ China, Dept Chem, Beijing 100872, Peoples R China
[2] Univ Liverpool, Dept Chem, Liverpool Ctr Mat & Catalysis, Liverpool L69 7ZD, Merseyside, England
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2010年 / 8卷 / 09期
基金：
中国国家自然科学基金;
关键词：
ELECTRON-RICH OLEFINS; OXIDATIVE HECK REACTIONS; CROSS-COUPLING REACTION; ENOL ETHERS; ACYL CHLORIDES; IONIC LIQUIDS; HETEROARYL HALIDES; ARYLBORONIC ACIDS; ROOM-TEMPERATURE; ALPHA-ARYLATION;
D O I：
10.1039/c001004a
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The combination of Pd(OAc)(2) with 1,3-bis(diphenylphosphino)propane (dppp) in ethylene glycol constitutes a high-performance catalytic system for highly regioselective arylation of a range of electron-rich vinyl ethers by aryl bromides to provide, upon hydrolysis, alkyl aryl ketones and cyclic ketals in good yields with up to 3.75 x 10(5) TON and 15625 h(-1) TOF.
引用
收藏
页码：2012 / 2015
页数：4
相关论文
共 50 条
  • [1] Direct synthesis of cyclic ketals of acetophenones by palladium-catalyzed arylation of hydroxyalkyl vinyl ethers
    Larhed, M
    Hallberg, A
    JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (22): : 7858 - 7862
  • [2] Palladium-Catalyzed Carbonylative Coupling of Aryl Iodides with Alkyl Bromides: Efficient Synthesis of Alkyl Aryl Ketones
    Peng, Jin-Bao
    Chen, Bo
    Qi, Xinxin
    Ying, Jun
    Wu, Xiao-Feng
    ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (21) : 4153 - 4160
  • [3] PALLADIUM-CATALYZED BETA-ARYLATION OF MODIFIED VINYL ETHERS WITH ARYL TRIFLATES
    BADONE, D
    GUZZI, U
    TETRAHEDRON LETTERS, 1993, 34 (22) : 3603 - 3606
  • [4] Palladium-catalyzed synthesis of α-aryl acetophenones from styryl ethers and aryl diazonium salts via regioselective Heck arylation at room temperature
    Venkatesh, Rapelly
    Singh, Adesh Kumar
    Lee, Yong Rok
    Kandasamy, Jeyakumar
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (36) : 7832 - 7837
  • [5] An efficient intermolecular palladium-catalyzed synthesis of aryl ethers
    Torraca, KE
    Huang, XH
    Parrish, CA
    Buchwald, SL
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (43) : 10770 - 10771
  • [6] PALLADIUM-CATALYZED ARYLATION OF ENOL ESTERS ETHERS AND HALIDES . A NEW SYNTHESIS OF 2-ARYL ALDEHYDES AND KETONES
    HECK, RF
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1968, 90 (20) : 5535 - &
  • [7] CHELATION-CONTROLLED, PALLADIUM-CATALYZED ARYLATION OF VINYL ETHERS
    LARHED, M
    ANDERSSON, CM
    HALLBERG, A
    ACTA CHEMICA SCANDINAVICA, 1993, 47 (02): : 212 - 217
  • [8] Palladium-catalyzed α-arylation of ketones
    Journal of the American Chemical Society, 1997, 119 (45):
  • [9] Palladium-catalyzed multiple arylation of phenyl ketones with aryl bromides
    Satoh, T
    Kametani, Y
    Terao, Y
    Miura, M
    Nomura, M
    TETRAHEDRON LETTERS, 1999, 40 (29) : 5345 - 5348
  • [10] PALLADIUM-CATALYZED ARYLATION OF UNSATURATED ACETALS AND KETALS
    ZEBOVITZ, TC
    HECK, RF
    JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (24): : 3907 - 3909
12345