Facile introduction of SH group on aromatic substrates via electrophilic substitution reactions

被引：28

作者：

Becht, JM ^{[1
]}

Wagner, A ^{[1
]}

Mioskowski, C ^{[1
]}

机构：

[1] Univ Strasbourg 1, UMR 7514 CNRS, Fac Pharm, Lab Synth Bioorgan, F-67400 Illkirch Graffenstaden, France

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2003年 / 68卷 / 14期

关键词：

D O I：

10.1021/jo034013h

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Herein, we describe a mild and efficient two-step procedure to introduce a thiol group on aromatic substrates. First, reaction with an activated sulfoxide leads to an arylsulfonium salt intermediate. Then, two successive beta-elimination-based dealkylation reactions afford the desired arylthiols in good to excellent yields.

引用

页码：5758 / 5761

页数：4

共 28 条

[1] SYNTHESIS OF ARYL-SUBSTITUTED SULFONIUM SALTS BY THE P2O5-METHANESULFONIC ACID PROMOTED CONDENSATION OF SULFOXIDES WITH AROMATIC-COMPOUNDS
AKHTAR, SR
CRIVELLO, JV
LEE, JL
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (13) : 4222 - 4225
[2] HIGH-YIELD BENZYNE SYNTHESIS OF DIARYL ETHERS
BATES, RB
JANDA, KD
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (22) : 4374 - 4376
[3] STUDY OF SRN1 REACTIONS .10. ACTION OF SULFANIONS ON FUNCTIONALIZED ARYL HALIDES - DIRECT SYNTHESIS OF BENZOTHIOPHENES AND THIENOPYRIDINES
BEUGELMANS, R
BOISCHOUSSY, M
BOUDET, B
[J]. TETRAHEDRON, 1983, 39 (24) : 4153 - 4161
[4] CABIDDU S, 1982, SYNTHESIS-STUTTGART, P583
[5] DEVASAGAYAM TP, 1991, J PHOTOCHEM PHOTOBIO, P105
[6] Sulfenate intermediates in the sulfoxide glycosylation reaction
Gildersleeve, J
Pascal, RA
Kahne, D
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (24) : 5961 - 5969
[7] GOETHALS E, 1964, B SOC CHIM BELG, V73, P546
[8] HOCKER J, 1975, SYNTHESIS-STUTTGART, P334
[9] Oriented immobilization of antibodies onto the gold surfaces via their native thiol groups
Karyakin, AA
Presnova, GV
Rubtsova, MY
Egorov, AM
[J]. ANALYTICAL CHEMISTRY, 2000, 72 (16) : 3805 - 3811
[10] Reversible inhibition of sheep liver sorbitol dehydrogenase by thiol compounds
Lindstad, RI
McKinleyMcKee, JS
[J]. EUROPEAN JOURNAL OF BIOCHEMISTRY, 1996, 241 (01): : 142 - 148

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