Borrowing hydrogen in the activation of alcohols

被引:1013
作者
Hamid, Malai Haniti S. A. [1 ]
Slatford, Paul A. [1 ]
Williams, Jonathan M. J. [1 ]
机构
[1] Univ Bath, Dept Chem, Bath BA2 7AY, Avon, England
基金
英国工程与自然科学研究理事会;
关键词
alcohols; amines; catalysis; transfer hydrogenation; transition metals;
D O I
10.1002/adsc.200600638
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
Alcohols can be temporarily converted into carbonyl compounds by the metal-catalysed removal of hydrogen. The carbonyl compounds are reactive in a wider range of transformations than the precursor alcohols and can react in situ to give imines, alkenes, and alpha-functionalised carbonyl compounds. The metal catalyst, which had borrowed the hydrogen, then returns it to the transformed carbonyl compound, leading to an overall process in which alcohols can be converted into amines, compounds containing C-C bonds and beta-functionalised alcohols.
引用
收藏
页码:1555 / 1575
页数:21
相关论文
共 164 条
[71]   Kinetic resolution of racemic secondary alcohols by Ru-II-catalyzed hydrogen transfer [J].
Hashiguchi, S ;
Fujii, A ;
Haack, KJ ;
Matsumura, K ;
Ikariya, T ;
Noyori, R .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1997, 36 (03) :288-290
[72]   Rhodium-catalysed racemisation of N-acyl α-amino acids [J].
Hateley, MJ ;
Schichl, DA ;
Kreuzfeld, HJ ;
Beller, M .
TETRAHEDRON LETTERS, 2000, 41 (20) :3821-3824
[73]   An improved ruthenium catalyst for the environmentally benign amination of primary and secondary alcohols [J].
Hollmann, Dirk ;
Tillack, Annegret ;
Michalik, Dirk ;
Jackstell, Ralf ;
Beller, Matthias .
CHEMISTRY-AN ASIAN JOURNAL, 2007, 2 (03) :403-410
[74]   Tishchenko reactions and Oppenauer oxidation reactions of aldehydes promoted by diisobutylaluminum hydride [J].
Hon, YS ;
Chang, CP ;
Wong, YC .
TETRAHEDRON LETTERS, 2004, 45 (16) :3313-3315
[75]   Alkylation and acetal formation using supercritical alcohol without catalyst [J].
Horikawa, Y ;
Uchino, Y ;
Sako, T .
CHEMISTRY LETTERS, 2003, 32 (03) :232-233
[76]   Stereoselective synthesis of δ-lactones from 5-oxoalkanals via one-pot sequential acetalization, tishchenko reaction, and lactonization by cooperative catalysis of samarium ion and mercaptan [J].
Hsu, JL ;
Fang, JM .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (25) :8573-8584
[77]   Cooperative catalysis of samarium diiodide and mercaptan in a stereoselective one-pot transformation of 5-oxopentanals into δ-lactones [J].
Hsu, JL ;
Chen, CT ;
Fang, JM .
ORGANIC LETTERS, 1999, 1 (12) :1989-1991
[78]   Racemisation in asymmetric synthesis.: Dynamic kinetic resolution and related processes in enzyme and metal catalysis [J].
Huerta, FF ;
Minidis, ABE ;
Bäckvall, JE .
CHEMICAL SOCIETY REVIEWS, 2001, 30 (06) :321-331
[79]  
HUH KT, 1990, B KOR CHEM SOC, V11, P45
[80]   RUTHENIUM CATALYZED N-METHYLATION OF AMINOARENES USING METHANOL [J].
HUH, KT ;
TSUJI, Y ;
KOBAYASHI, M ;
OKUDA, F ;
WATANABE, Y .
CHEMISTRY LETTERS, 1988, (03) :449-452