Ruthenium-catalyzed one-pot β-alkylation of secondary alcohols with primary alcohols

被引:159
作者
Cho, CS [1 ]
Kim, BT
Kim, HS
Kim, TJ
Shim, SC
机构
[1] Kyungpook Natl Univ, Res Inst Ind Technol, Taegu 702701, South Korea
[2] Kyungpook Natl Univ, Coll Engn, Dept Ind Chem, Taegu 702701, South Korea
关键词
D O I
10.1021/om030307h
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Secondary alcohols (carbinols) react with primary alcohols in dioxane at 80 degreesC in the presence of a catalytic amount of RUCl2(PPh3)(3) and KOH along with a sacrificial hydrogen acceptor to afford the corresponding coupled secondary alcohols. The reaction is applicable to a wide range of aryl methyl, alkyl methyl, and cyclic carbinols, and with alkyl methyl carbinols, the alkylation took place exclusively at the less-hindered methyl position over beta-methylene and -methine.
引用
收藏
页码:3608 / 3610
页数:3
相关论文
共 27 条
[1]   APPLICATIONS OF AMMONIUM FORMATE CATALYTIC TRANSFER HYDROGENATION .6. ANALYSIS OF CATALYST, DONOR QUANTITY, AND SOLVENT EFFECTS UPON THE EFFICACY OF DECHLORINATION [J].
ANWER, MK ;
SHERMAN, DB ;
RONEY, JG ;
SPATOLA, AF .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (06) :1284-1289
[2]  
Backball J.-E., 1992, PERSPECTIVES COORDIN, P463
[3]   H-TRANSFER CATALYSIS WITH RU3(CO)12 [J].
BLUM, Y ;
RESHEF, D ;
SHVO, Y .
TETRAHEDRON LETTERS, 1981, 22 (16) :1541-1544
[4]  
Caine D., 1991, Comprehensive Organic Synthesis, V3, P1
[5]   Synthesis of quinolines via ruthenium-catalysed amine exchange reaction between anilines and trialkylamines [J].
Cho, CS ;
Oh, BH ;
Kim, JS ;
Kim, TJ ;
Shim, SC .
CHEMICAL COMMUNICATIONS, 2000, (19) :1885-1886
[6]   Ruthenium-catalyzed regioselective synthesis of 2-substituted indoles via ring-opening of epoxides by anilines [J].
Cho, CS ;
Kim, JH ;
Choi, HJ ;
Kim, TJ ;
Shim, SC .
TETRAHEDRON LETTERS, 2003, 44 (14) :2975-2977
[7]   Ruthenium-catalyzed regioselective α-alkylation of ketones with primary alcohols [J].
Cho, CS ;
Kim, BT ;
Kim, TJ ;
Shim, SC .
TETRAHEDRON LETTERS, 2002, 43 (44) :7987-7989
[8]   An unusual type of ruthenium-catalyzed transfer hydrogenation of ketones with alcohols accompanied by C-C coupling [J].
Cho, CS ;
Kim, BT ;
Kim, TJ ;
Shim, SC .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (26) :9020-9022
[9]   Ruthenium-catalysed oxidative cyclisation of 2-aminobenzyl alcohol with ketones: modified Friedlaender quinoline synthesis [J].
Cho, CS ;
Kim, BT ;
Kim, TJ ;
Shim, SC .
CHEMICAL COMMUNICATIONS, 2001, (24) :2576-2577
[10]   Ruthenium-catalyzed reductive cyclization of nitroarenes with trialkylamines leading to quinolines [J].
Cho, CS ;
Kim, TK ;
Kim, BT ;
Kim, TJ ;
Shim, SC .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2002, 650 (1-2) :65-68