Synthesis of α-Hydroxy Carboxylic Acids via a Nickel(II)-Catalyzed Hydrogen Transfer Process

被引：35
作者：
Tang, Guo [1 ,2 ]
Cheng, Chien-Hong [1 ]
机构：
[1] Natl Tsing Hua Univ, Dept Chem, Hsinchu 30013, Taiwan
[2] Xiamen Univ, Dept Chem, Coll Chem & Chem Engn, Xiamen 361005, Fujian, Peoples R China
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2011年 / 353卷 / 11-12期
关键词：
hydrogen transfer process; alpha-hydroxy carboxylic acids; lactic acid; nickel-catalyzed reaction; primary alcohols; PASSERINI-TYPE REACTIONS; SECONDARY ALCOHOLS; BETA-ALKYLATION; KINETIC RESOLUTION; AROMATIC-ALDEHYDES; NICKEL-COMPLEXES; EFFICIENT ROUTE; CYCLIZATION; ISOCYANIDES; DERIVATIVES;
D O I：
10.1002/adsc.201100241
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
A new catalytic system for beta-alkylation of lactic acid with primary alcohols has been developed. In the presence of nickel(II) acetate tetrahydrate [Ni(OAc)(2)(H(2)O)(4)] and base, lactic acid reacts with primary alcohols to afford the corresponding coupled alpha-hydroxy carboxylic acids in good to excellent yields via a hydrogen transfer process without any hydrogen acceptor or hydrogen donor.
引用
收藏
页码：1918 / 1922
页数：5
相关论文
共 35 条
  • [1] Green alcohol couplings without transition metal catalysts: base-mediated β-alkylation of alcohols in aerobic conditions
    Allen, Laura J.
    Crabtree, Robert H.
    [J]. GREEN CHEMISTRY, 2010, 12 (08) : 1362 - 1364
  • [2] [Anonymous], 2007, Angew. Chem.
  • [3] Ruthenium-Catalyzed β-Alkylation of Secondary Alcohols with Primary Alcohols
    Cheung, Hung Wai
    Lee, Ting Yan
    Lui, Ho Yin
    Yeung, Chi Hung
    Lau, Chak Po
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2008, 350 (18) : 2975 - 2983
  • [4] Ruthenium-catalyzed one-pot β-alkylation of secondary alcohols with primary alcohols
    Cho, CS
    Kim, BT
    Kim, HS
    Kim, TJ
    Shim, SC
    [J]. ORGANOMETALLICS, 2003, 22 (17) : 3608 - 3610
  • [5] An unusual type of ruthenium-catalyzed transfer hydrogenation of ketones with alcohols accompanied by C-C coupling
    Cho, CS
    Kim, BT
    Kim, TJ
    Shim, SC
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (26) : 9020 - 9022
  • [6] Catalytic, enantioselective α-additions of isocyanides:: Lewis base catalyzed Passerini-type reactions
    Denmark, SE
    Fan, Y
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (24) : 9667 - 9676
  • [7] The first catalytic, asymmetric α-additions of isocyanides.: Lewis-base-catalyzed, enantioselective Passerini-type reactions
    Denmark, SE
    Fan, Y
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (26) : 7825 - 7827
  • [8] Dehydrogenation as a Substrate-Activating Strategy in Homogeneous Transition-Metal Catalysis
    Dobereiner, Graham E.
    Crabtree, Robert H.
    [J]. CHEMICAL REVIEWS, 2010, 110 (02) : 681 - 703
  • [9] Direct β-alkylation of secondary alcohols with primary alcohols catalyzed by a Cp*lr complex
    Fujita, K
    Asai, C
    Yamaguchi, T
    Hanasaka, F
    Yamaguchi, R
    [J]. ORGANIC LETTERS, 2005, 7 (18) : 4017 - 4019
  • [10] Alcohols as electrophiles in C-C bond-forming reactions:: The hydrogen autotransfer process
    Guillena, Gabriela
    Ramon, Diego J.
    Yus, Miguel
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (14) : 2358 - 2364
1234