Copper(II) tetrafluoroborate as a novel and highly efficient catalyst for Michael addition of mercaptans to α,β-unsaturated carbonyl compounds

被引：120

作者：

Garg, SK ^{[1
]}

Kumar, R ^{[1
]}

Chakraborti, AK ^{[1
]}

机构：

[1] NIPER, Dept Med Chem, Nagar 160062, Punjab, India

来源：

TETRAHEDRON LETTERS | 2005年 / 46卷 / 10期

关键词：

Michael addition; thiol; alpha; beta-unsaturated carbonyl; copper(II) tetrafluoroborate; catalyst;

D O I：

10.1016/j.tetlet.2005.01.051

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Copper(II) tetrafluoroborate has been found to be a new and highly efficient catalyst for Michael addition of thiols to alpha,beta-unsaturated carbonyl compounds under solvent-free conditions and in H2O at room temperature. The reactions are very fast and are completed in 2 min to 1 h affording high yields. The rate of thiol addition was dependent on the steric hindrance at the beta-carbon of the alpha,beta-unsaturated carbonyl substrate. In the case of chalcones, the reactions are best carried out in MeOH as solvent. (C) 2005 Elsevier Ltd. All rights reserved.

引用

页码：1721 / 1724

页数：4

共 22 条

[1] A natural phosphate and doped-catalyzed Michael addition of mercaptans to α,β-unsaturated carbonyl compounds
Abrouki, Y
Zahouily, M
Rayadh, A
Bahlaouan, B
Sebti, S
[J]. TETRAHEDRON LETTERS, 2002, 43 (49) : 8951 - 8953
[2] Conjugate addition of indoles and thiols with electron-deficient olefins catalyzed by Bi(OTf)3
Alam, MM
Varala, R
Adapa, SR
[J]. TETRAHEDRON LETTERS, 2003, 44 (27) : 5115 - 5119
[3] [Anonymous], AM CHEM SOC S SERIES
[4] OXIDATIVE FUNCTIONALIZATION OF THE BETA-CARBON IN ALPHA,BETA-UNSATURATED SYSTEMS - PREPARATION OF 3-PHENYLTHIO ENONES, ACRYLATES, AND OTHER VINYL DERIVATIVES
BAKUZIS, P
BAKUZIS, MLF
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (02) : 235 - 239
[5] Sequential one-pot InBr3-catalyzed 1,4-then 1,2-nucleophilic addition to enones
Bandini, M
Cozzi, PG
Giacomini, M
Melchiorre, P
Selva, S
Umani-Ronchi, A
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (11) : 3700 - 3704
[6] Copper(II) tetrafluoroborate-catalyzed formation of aldehyde-1,1-diacetates
Chakraborti, AK
Thilagavathi, R
Kumar, R
[J]. SYNTHESIS-STUTTGART, 2004, (06): : 831 - 833
[7] Chakraborti AK, 2004, SYNTHESIS-STUTTGART, P111
[8] An alumina-catalyzed Michael addition of mercaptans to N-anilinomaleimides and its application to the solution-phase parallel synthesis of libraries
Cheng, S
Comer, DD
[J]. TETRAHEDRON LETTERS, 2002, 43 (07) : 1179 - 1181
[9] CARBONYL-PROTECTED BETA-LITHIO ALDEHYDES AND KETONES VIA REDUCTIVE LITHIATION - A GENERAL PREPARATIVE METHOD FOR REMARKABLY VERSATILE HOMOENOLATE EQUIVALENTS
CHERKAUSKAS, JP
COHEN, T
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (01) : 6 - 8
[10] REMOVAL OF SULFUR GROUPS FROM MOLECULES BY COPPER(I) - PREPARATION OF SULFUR-SUBSTITUTED 1,3-DIENES FOR DIELS-ALDER REACTION
COHEN, T
MURA, AJ
SHULL, DW
FOGEL, ER
RUFFNER, RJ
FALCK, JR
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (19) : 3218 - 3219

← 1 2 3 →