Palladium-Catalyzed Carbonylative Esterification of Primary Alcohols with Aryl Chlorides through Dehydroxymethylative C-C Bond Cleavage

被引:27
|
作者
Park, Hyo-Soon [1 ]
Kim, Dong-Su [1 ]
Jun, Chul-Ho [1 ]
机构
[1] Yonsei Univ, Dept Chem, Seoul 120749, South Korea
来源
ACS CATALYSIS | 2015年 / 5卷 / 01期
基金
新加坡国家研究基金会;
关键词
C-C activation; carbonylative esterification; catalysis; decarbonylation; palladium; CARBON-CARBON BONDS; COUPLING REACTIONS; METAL INSERTION; HALIDES; FORMATE; HYDROESTERIFICATION; DECARBONYLATION; ACTIVATION; ALDEHYDES; ALKYL;
D O I
10.1021/cs501778q
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
Aryl chlorides in the presence of Pd/C catalyst and NaF react with primary alcohols to form esters, arenes, and alkanes. In this reaction, aryl chlorides act as both oxidants and coupling partners, whereas alcohols serve as both carbonyl sources and alkoxy components of the ester products
引用
收藏
页码:397 / 401
页数:5
相关论文
共 50 条
  • [1] Palladium-Catalyzed Allylic Esterification via C-C Bond Cleavage of a Secondary Homoallyl Alcohol
    Wang, Yong
    Kang, Qiang
    [J]. ORGANIC LETTERS, 2014, 16 (16) : 4190 - 4193
  • [2] Palladium-catalyzed C-H bond arylation with aryl chlorides
    Chiong, Hendrich A.
    Daugulis, Olafs
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2007, 233
  • [3] Palladium-catalyzed C-C bond cleavage of N-cyclopropyl acylhydrazones
    Fujioka, Hiroki
    Yasui, Motohiro
    Hamada, Shohei
    Fukumi, Kohei
    Takeda, Norihiko
    Kobayashi, Yusuke
    Furuta, Takumi
    Ueda, Masafumi
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2024, 22 (16) : 3262 - 3267
  • [4] Palladium-catalyzed carbonylative transformation of aryl chlorides and aryl tosylates
    Wu, Xiao-Feng
    [J]. RSC ADVANCES, 2016, 6 (87): : 83831 - 83837
  • [5] Palladium-catalyzed gaseous CO-free carbonylative C-C bond activation of cyclobutanones
    Song, Kun-Long
    Wu, Bin
    Gan, Wan-Er
    Yang, Wan-Chun
    Chen, Xiao-Bing
    Cao, Jian
    Xu, Li-Wen
    [J]. ORGANIC CHEMISTRY FRONTIERS, 2021, 8 (13): : 3398 - 3403
  • [6] Functionalized styrene synthesis via palladium-catalyzed C-C cleavage of aryl ketones
    Zhang, Xu
    Wang, Zhen-Yu
    Wang, Xing
    Xu, Hui
    Dai, Hui-Xiong
    [J]. TETRAHEDRON LETTERS, 2022, 95
  • [7] Palladium-catalyzed intramolecular rearrangement of vinylidenecyclopropanes through C-C bond activation
    Pan, Dong
    Chen, Gen-Qiang
    Tang, Xiang-Ying
    Shi, Min
    [J]. ORGANIC CHEMISTRY FRONTIERS, 2015, 2 (07): : 792 - 796
  • [8] CO/C-H as an Acylating Reagent: A Palladium-Catalyzed Aerobic Oxidative Carbonylative Esterification of Alcohols
    Wang, Lu
    Wang, Yanxia
    Liu, Chao
    Lei, Aiwen
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (22) : 5657 - 5661
  • [9] Palladium-Catalyzed Skeletal Rearrangement of Cyclobutanones via C-H and C-C Bond Cleavage
    Ano, Yusuke
    Takahashi, Daichi
    Yamada, Yuki
    Chatani, Naoto
    [J]. ACS CATALYSIS, 2023, 13 (04) : 2234 - 2239
  • [10] Palladium-Catalyzed Skeletal Reorganization of Cyclobutanones Invoving Successive C-C Bond/C-H Bond Cleavage
    Li, Ruirui
    Shi, Xiaonan
    Zhao, Dongbing
    [J]. CHINESE JOURNAL OF CHEMISTRY, 2023, 41 (14) : 1679 - 1683