Palladium-Catalyzed Reduction of Acid Chlorides to Aldehydes with Hydrosilanes

被引:16
|
作者
Fujihara, Tetsuaki [1 ]
Cong, Cong [1 ]
Iwai, Tomohiro [1 ]
Terao, Jun [1 ]
Tsuji, Yasushi [1 ]
机构
[1] Kyoto Univ, Grad Sch Engn, Dept Energy & Hydrocarbon Chem, Nishikyo Ku, Kyoto 6158510, Japan
关键词
acid chloride; aldehyde; hydrosilane; palladium; phosphine; TRI-TERT-BUTOXYALUMINOHYDRIDE; ACYL CHLORIDES; ORGANOSILICON HYDRIDES; SODIUM-BOROHYDRIDE; RHODIUM COMPLEXES; TERMINAL ALKYNES; CONVERSION; HYDROSILYLATION; PLATINUM; HALIDES;
D O I
10.1055/s-0032-1317155
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient synthesis of aldehydes from acid chlorides with hydrosilanes as a reducing agent in the presence of a palladium catalyst has been achieved. A simple mixture of commercially available Pd(dba)(2) and Mes(3)P as a catalyst realized the reduction of various acid chlorides including aliphatic acid chlorides and alpha,beta-unsaturated acid chlorides to the corresponding aldehydes in good to high yields under mild reaction conditions.
引用
收藏
页码:2389 / 2392
页数:4
相关论文
共 50 条
  • [1] Iron oxide catalyzed reduction of acid chlorides to aldehydes with hydrosilanes
    Cong, Cong
    Fujihara, Tetsuaki
    Terao, Jun
    Tsuji, Yasushi
    CATALYSIS COMMUNICATIONS, 2014, 50 : 25 - 28
  • [2] Palladium-Catalyzed Formal Hydroacylation of Allenes Employing Acid Chlorides and Hydrosilanes
    Fujihara, Tetsuaki
    Tatsumi, Kenta
    Terao, Jun
    Tsuji, Yasushi
    ORGANIC LETTERS, 2013, 15 (09) : 2286 - 2289
  • [3] Palladium-Catalyzed Reduction of Carboxylic Acids to Aldehydes with Hydrosilanes in the Presence of Pivalic Anhydride
    Fujihara, Tetsuaki
    Cong, Cong
    Terao, Jun
    Tsuji, Yasushi
    ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (17) : 3420 - 3424
  • [4] PALLADIUM-CATALYZED REDUCTION OF ACYL CHLORIDES WITH TRIBUTYLGERMANIUM HYDRIDE
    GENG, LF
    LU, XY
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1989, 376 (01) : 41 - 43
  • [5] A new synthesis of aldehydes by the palladium-catalyzed reaction of 2-pyridinyl esters with hydrosilanes
    Nakanishi, J
    Tatamidani, H
    Fukumoto, Y
    Chatani, N
    SYNLETT, 2006, (06) : 869 - 872
  • [6] PALLADIUM-CATALYZED REACTION OF TRIBUTYLTIN HYDRIDE WITH ACYL CHLORIDES - A SELECTIVE ROUTE TO ALDEHYDES
    GUIBE, F
    FOUR, P
    RIVIERE, H
    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1980, (10) : 432 - 433
  • [7] Acid anhydrides as alternatives to acid chlorides in the palladium-catalyzed reaction with silacyclobutanes
    Tanaka, Y
    Yamashita, M
    APPLIED ORGANOMETALLIC CHEMISTRY, 2002, 16 (01) : 51 - 54
  • [8] Palladium-Catalyzed Decarbonylative Difluoromethylation of Acid Chlorides at Room Temperature
    Pan, Fei
    Boursalian, Gregory B.
    Ritter, Tobias
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (51) : 16871 - 16876
  • [9] Palladium-catalyzed reactions of arylboron compounds with carboxylic acid chlorides
    Korolev, DN
    Bumagin, NA
    RUSSIAN CHEMICAL BULLETIN, 2004, 53 (02) : 364 - 369
  • [10] Palladium-catalyzed regiodivergent hydrochlorocarbonylation of alkenes for formation of acid chlorides
    Wu, Fei
    Wang, Bo
    Li, Na-Qi
    Yang, Hui-Yi
    Ren, Zhi-Hui
    Guan, Zheng-Hui
    NATURE COMMUNICATIONS, 2023, 14 (01)