A palladium-catalyzed route for α-alkylation of ketones by primary alcohols

被引：109

作者：

Cho, CS ^{[1
]}

机构：

[1] Kyungpook Natl Univ, Ind Technol Res Inst, Taegu 702701, South Korea

来源：

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL | 2005年 / 240卷 / 1-2期

关键词：

alpha-alkylation; hydrogen acceptor; ketoncs; palladium catalysts; primary alcohols;

D O I：

10.1016/j.molcata.2005.06.043

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：

Ketones react with primary alcohols in dioxane at 100 degrees C in the presence of a catalytic amount of Pd/C and KOH along with 1-decene as a sacrificial hydrogen acceptor to give the corresponding coupled ketones in moderate to good yields. The catalytic pathway seems to be proceeded via a sequence involving initial oxidation of primary alcohols to aldehydes, cross aldol condensation, and regioselective reduction. (c) 2005 Elsevier B.V. All rights reserved.

引用

页码：55 / 60

页数：6

共 41 条

[1] Facile and efficient synthesis of pyrroles and indoles via palladium-catalyzed oxidation of hydroxy-enamines and -amines [J].

Aoyagi, Y ;

Mizusaki, T ;

Ohta, A .

TETRAHEDRON LETTERS, 1996, 37 (51) :9203-9206

[2]

Backball J.-E., 1992, PERSPECTIVES COORDIN, P463

[3]

Caine D., 1991, Comprehensive Organic Synthesis, V3, P1

[4] Palladium-catalyzed addition of ketones to alkylidenecyclopropanes [J].

Camacho, DH ;

Nakamura, I ;

Oh, BH ;

Saito, S ;

Yamamoto, Y .

TETRAHEDRON LETTERS, 2002, 43 (16) :2903-2907

[5] Ruthenium-catalyzed oxidative coupling and cyclization between 2-aminobenzyl alcohol and secondary alcohols leading to quinolines [J].

Cho, CS ;

Kim, BT ;

Choi, HJ ;

Kim, TJ ;

Shim, SC .

TETRAHEDRON, 2003, 59 (40) :7997-8002

[6] Palladium-catalyzed tandem Heck and aldol reactions between 2-bromobenzaldehydes and functionalized alkenes leading to naphthalenes [J].

Cho, CS ;

Lim, DK ;

Zhang, JQ ;

Kim, TJ ;

Shim, SC .

TETRAHEDRON LETTERS, 2004, 45 (29) :5653-5656

[7] Facile palladium-catalysed synthesis of 1-aryl-1H-indazoles from 2-bromobenzaldehydes and arylhydrazines [J].

Cho, CS ;

Lim, DK ;

Heo, NH ;

Kim, TJ ;

Shim, SC .

CHEMICAL COMMUNICATIONS, 2004, (01) :104-105

[8] Ruthenium-catalyzed one-pot β-alkylation of secondary alcohols with primary alcohols [J].

Cho, CS ;

Kim, BT ;

Kim, HS ;

Kim, TJ ;

Shim, SC .

ORGANOMETALLICS, 2003, 22 (17) :3608-3610

[9] 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

[10] 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

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