共 45 条
Perchloric acid impregnated on silica gel (HClO4/SiO2):: A versatile catalyst for Michael addition of thiols to the electron-deficient alkenes
被引:72
作者:

Khan, Abu T.
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Indian Inst Technol, Dept Chem, Gauhati 781039, India Indian Inst Technol, Dept Chem, Gauhati 781039, India

Ghosh, Subrata
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机构:
Indian Inst Technol, Dept Chem, Gauhati 781039, India Indian Inst Technol, Dept Chem, Gauhati 781039, India

Choudhury, Lokman H.
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Indian Inst Technol, Dept Chem, Gauhati 781039, India Indian Inst Technol, Dept Chem, Gauhati 781039, India
机构:
[1] Indian Inst Technol, Dept Chem, Gauhati 781039, India
关键词:
Thiols;
electron-deficient alkenes;
Michael addition;
silica-supported perchloric acid;
D O I:
10.1002/ejoc.200600006
中图分类号:
O62 [有机化学];
学科分类号:
070303 ;
081704 ;
摘要:
Perchloric acid adsorbed on silica gel (HClO4/SiO2) has been found to be a highly efficient and versatile catalyst for the Michael addition of thiols to a wide variety of conjugated alkenes such as alpha,beta-unsaturated ketones, carboxylic esters, nitriles, amides and chalcones in dichloromethane or methanol at room temperature. The reactions are completed within 2-20 min in high yields. Some of the additional advantages are: no aqueous work-up is necessary, and the catalyst is also reusable. Moreover, the solid product can be obtained without chromatographic separation.
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页码:2226 / 2231
页数:6
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[1]
A natural phosphate and doped-catalyzed Michael addition of mercaptans to α,β-unsaturated carbonyl compounds
[J].
Abrouki, Y
;
Zahouily, M
;
Rayadh, A
;
Bahlaouan, B
;
Sebti, S
.
TETRAHEDRON LETTERS,
2002, 43 (49)
:8951-8953

Abrouki, Y
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Hassan 2, Fac Sci & Tech, UFR Chim Appliquee, Lab Synthese Organ & Traitement Informat, Mohammadia 20650, Morocco Univ Hassan 2, Fac Sci & Tech, UFR Chim Appliquee, Lab Synthese Organ & Traitement Informat, Mohammadia 20650, Morocco

Zahouily, M
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Hassan 2, Fac Sci & Tech, UFR Chim Appliquee, Lab Synthese Organ & Traitement Informat, Mohammadia 20650, Morocco Univ Hassan 2, Fac Sci & Tech, UFR Chim Appliquee, Lab Synthese Organ & Traitement Informat, Mohammadia 20650, Morocco

Rayadh, A
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Hassan 2, Fac Sci & Tech, UFR Chim Appliquee, Lab Synthese Organ & Traitement Informat, Mohammadia 20650, Morocco Univ Hassan 2, Fac Sci & Tech, UFR Chim Appliquee, Lab Synthese Organ & Traitement Informat, Mohammadia 20650, Morocco

Bahlaouan, B
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Hassan 2, Fac Sci & Tech, UFR Chim Appliquee, Lab Synthese Organ & Traitement Informat, Mohammadia 20650, Morocco Univ Hassan 2, Fac Sci & Tech, UFR Chim Appliquee, Lab Synthese Organ & Traitement Informat, Mohammadia 20650, Morocco

Sebti, S
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Hassan 2, Fac Sci & Tech, UFR Chim Appliquee, Lab Synthese Organ & Traitement Informat, Mohammadia 20650, Morocco Univ Hassan 2, Fac Sci & Tech, UFR Chim Appliquee, Lab Synthese Organ & Traitement Informat, Mohammadia 20650, Morocco
[2]
Protic acid (HClO4 supported on silica gel)-mediated synthesis of 2,3-unsaturated-O-glucosides and a chiral furan diol from 2,3-glycals
[J].
Agarwal, A
;
Rani, S
;
Vankar, YD
.
JOURNAL OF ORGANIC CHEMISTRY,
2004, 69 (18)
:6137-6140

Agarwal, A
论文数: 0 引用数: 0
h-index: 0
机构:
Indian Inst Technol, Dept Chem, Kanpur 208016, Uttar Pradesh, India Indian Inst Technol, Dept Chem, Kanpur 208016, Uttar Pradesh, India

Rani, S
论文数: 0 引用数: 0
h-index: 0
机构:
Indian Inst Technol, Dept Chem, Kanpur 208016, Uttar Pradesh, India Indian Inst Technol, Dept Chem, Kanpur 208016, Uttar Pradesh, India

Vankar, YD
论文数: 0 引用数: 0
h-index: 0
机构:
Indian Inst Technol, Dept Chem, Kanpur 208016, Uttar Pradesh, India Indian Inst Technol, Dept Chem, Kanpur 208016, Uttar Pradesh, India
[3]
Conjugate addition of indoles and thiols with electron-deficient olefins catalyzed by Bi(OTf)3
[J].
Alam, MM
;
Varala, R
;
Adapa, SR
.
TETRAHEDRON LETTERS,
2003, 44 (27)
:5115-5119

Alam, MM
论文数: 0 引用数: 0
h-index: 0
机构:
Indian Inst Chem Technol, Inorgan Chem Div, Hyderabad 500007, Andhra Pradesh, India Indian Inst Chem Technol, Inorgan Chem Div, Hyderabad 500007, Andhra Pradesh, India

Varala, R
论文数: 0 引用数: 0
h-index: 0
机构:
Indian Inst Chem Technol, Inorgan Chem Div, Hyderabad 500007, Andhra Pradesh, India Indian Inst Chem Technol, Inorgan Chem Div, Hyderabad 500007, Andhra Pradesh, India

Adapa, SR
论文数: 0 引用数: 0
h-index: 0
机构:
Indian Inst Chem Technol, Inorgan Chem Div, Hyderabad 500007, Andhra Pradesh, India Indian Inst Chem Technol, Inorgan Chem Div, Hyderabad 500007, Andhra Pradesh, India
[4]
Sequential one-pot InBr3-catalyzed 1,4-then 1,2-nucleophilic addition to enones
[J].
Bandini, M
;
Cozzi, PG
;
Giacomini, M
;
Melchiorre, P
;
Selva, S
;
Umani-Ronchi, A
.
JOURNAL OF ORGANIC CHEMISTRY,
2002, 67 (11)
:3700-3704

Bandini, M
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Bologna, Dipartimento Chim G Ciamician, I-40126 Bologna, Italy Univ Bologna, Dipartimento Chim G Ciamician, I-40126 Bologna, Italy

Cozzi, PG
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Bologna, Dipartimento Chim G Ciamician, I-40126 Bologna, Italy Univ Bologna, Dipartimento Chim G Ciamician, I-40126 Bologna, Italy

Giacomini, M
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Bologna, Dipartimento Chim G Ciamician, I-40126 Bologna, Italy Univ Bologna, Dipartimento Chim G Ciamician, I-40126 Bologna, Italy

论文数: 引用数:
h-index:
机构:

Selva, S
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Bologna, Dipartimento Chim G Ciamician, I-40126 Bologna, Italy Univ Bologna, Dipartimento Chim G Ciamician, I-40126 Bologna, Italy

Umani-Ronchi, A
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Bologna, Dipartimento Chim G Ciamician, I-40126 Bologna, Italy Univ Bologna, Dipartimento Chim G Ciamician, I-40126 Bologna, Italy
[5]
Perchloric acid adsorbed on silica gel as a new, highly efficient, and versatile catalyst for acetylation of phenols, thiols, alcohols, and amines
[J].
Chakraborti, AK
;
Gulhane, R
.
CHEMICAL COMMUNICATIONS,
2003, (15)
:1896-1897

Chakraborti, AK
论文数: 0 引用数: 0
h-index: 0
机构:
NIPER, Dept Med Chem, SAS Nagar 160062, Punjab, India NIPER, Dept Med Chem, SAS Nagar 160062, Punjab, India

Gulhane, R
论文数: 0 引用数: 0
h-index: 0
机构:
NIPER, Dept Med Chem, SAS Nagar 160062, Punjab, India NIPER, Dept Med Chem, SAS Nagar 160062, Punjab, India
[6]
Iodine-catalyzed Michael addition of mercaptans to α,β-unsaturated ketones under solvent-free conditions
[J].
Chu, CM
;
Gao, SJ
;
Sastry, MNV
;
Yao, CF
.
TETRAHEDRON LETTERS,
2005, 46 (30)
:4971-4974

Chu, CM
论文数: 0 引用数: 0
h-index: 0
机构:
Natl Taiwan Normal Univ, Dept Chem, Taipei 116, Taiwan Natl Taiwan Normal Univ, Dept Chem, Taipei 116, Taiwan

Gao, SJ
论文数: 0 引用数: 0
h-index: 0
机构:
Natl Taiwan Normal Univ, Dept Chem, Taipei 116, Taiwan Natl Taiwan Normal Univ, Dept Chem, Taipei 116, Taiwan

Sastry, MNV
论文数: 0 引用数: 0
h-index: 0
机构:
Natl Taiwan Normal Univ, Dept Chem, Taipei 116, Taiwan Natl Taiwan Normal Univ, Dept Chem, Taipei 116, Taiwan

Yao, CF
论文数: 0 引用数: 0
h-index: 0
机构:
Natl Taiwan Normal Univ, Dept Chem, Taipei 116, Taiwan Natl Taiwan Normal Univ, Dept Chem, Taipei 116, Taiwan
[7]
REMOVAL OF SULFUR GROUPS FROM MOLECULES BY COPPER(I) - PREPARATION OF SULFUR-SUBSTITUTED 1,3-DIENES FOR DIELS-ALDER REACTION
[J].
COHEN, T
;
MURA, AJ
;
SHULL, DW
;
FOGEL, ER
;
RUFFNER, RJ
;
FALCK, JR
.
JOURNAL OF ORGANIC CHEMISTRY,
1976, 41 (19)
:3218-3219

COHEN, T
论文数: 0 引用数: 0
h-index: 0
机构:
UNIV PITTSBURGH,DEPT CHEM,PITTSBURGH,PA 15260 UNIV PITTSBURGH,DEPT CHEM,PITTSBURGH,PA 15260

MURA, AJ
论文数: 0 引用数: 0
h-index: 0
机构:
UNIV PITTSBURGH,DEPT CHEM,PITTSBURGH,PA 15260 UNIV PITTSBURGH,DEPT CHEM,PITTSBURGH,PA 15260

SHULL, DW
论文数: 0 引用数: 0
h-index: 0
机构:
UNIV PITTSBURGH,DEPT CHEM,PITTSBURGH,PA 15260 UNIV PITTSBURGH,DEPT CHEM,PITTSBURGH,PA 15260

FOGEL, ER
论文数: 0 引用数: 0
h-index: 0
机构:
UNIV PITTSBURGH,DEPT CHEM,PITTSBURGH,PA 15260 UNIV PITTSBURGH,DEPT CHEM,PITTSBURGH,PA 15260

RUFFNER, RJ
论文数: 0 引用数: 0
h-index: 0
机构:
UNIV PITTSBURGH,DEPT CHEM,PITTSBURGH,PA 15260 UNIV PITTSBURGH,DEPT CHEM,PITTSBURGH,PA 15260

FALCK, JR
论文数: 0 引用数: 0
h-index: 0
机构:
UNIV PITTSBURGH,DEPT CHEM,PITTSBURGH,PA 15260 UNIV PITTSBURGH,DEPT CHEM,PITTSBURGH,PA 15260
[8]
ASYMMETRIC SYNTHESES BASED ON 1,3-OXATHIANES .1. SCOPE OF THE REACTION
[J].
ELIEL, EL
;
MORRISNATSCHKE, S
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
1984, 106 (10)
:2937-2942

ELIEL, EL
论文数: 0 引用数: 0
h-index: 0

MORRISNATSCHKE, S
论文数: 0 引用数: 0
h-index: 0
[9]
A catalytic Michael addition of thiols to α,β-unsaturated carbonyl compounds:: Asymmetric Michael additions and asymmetric protonations
[J].
Emori, E
;
Arai, T
;
Sasai, H
;
Shibasaki, M
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
1998, 120 (16)
:4043-4044

Emori, E
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Tokyo, Grad Sch Pharmaceut Sci, Bunkyo Ku, Tokyo 1130033, Japan Univ Tokyo, Grad Sch Pharmaceut Sci, Bunkyo Ku, Tokyo 1130033, Japan

Arai, T
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Tokyo, Grad Sch Pharmaceut Sci, Bunkyo Ku, Tokyo 1130033, Japan Univ Tokyo, Grad Sch Pharmaceut Sci, Bunkyo Ku, Tokyo 1130033, Japan

Sasai, H
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Tokyo, Grad Sch Pharmaceut Sci, Bunkyo Ku, Tokyo 1130033, Japan Univ Tokyo, Grad Sch Pharmaceut Sci, Bunkyo Ku, Tokyo 1130033, Japan

Shibasaki, M
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Tokyo, Grad Sch Pharmaceut Sci, Bunkyo Ku, Tokyo 1130033, Japan Univ Tokyo, Grad Sch Pharmaceut Sci, Bunkyo Ku, Tokyo 1130033, Japan
[10]
[HP(HNCH2CH2)3N]NO3:: an efficient homogeneous and solid-supported promoter for aza and thia-Michael reactions and for Strecker reactions
[J].
Fetterly, BA
;
Jana, NK
;
Verkade, JG
.
TETRAHEDRON,
2006, 62 (2-3)
:440-456

Fetterly, BA
论文数: 0 引用数: 0
h-index: 0
机构:
Iowa State Univ Sci & Technol, Dept Chem, 1605 Gilman Hall, Ames, IA 50011 USA Iowa State Univ Sci & Technol, Dept Chem, 1605 Gilman Hall, Ames, IA 50011 USA

Jana, NK
论文数: 0 引用数: 0
h-index: 0
机构:
Iowa State Univ Sci & Technol, Dept Chem, 1605 Gilman Hall, Ames, IA 50011 USA Iowa State Univ Sci & Technol, Dept Chem, 1605 Gilman Hall, Ames, IA 50011 USA

Verkade, JG
论文数: 0 引用数: 0
h-index: 0
机构:
Iowa State Univ Sci & Technol, Dept Chem, 1605 Gilman Hall, Ames, IA 50011 USA Iowa State Univ Sci & Technol, Dept Chem, 1605 Gilman Hall, Ames, IA 50011 USA