Hydrothiolation of unactivated Alkynes catalyzed by indium(III) bromide

被引：32

作者：

Yadav, J. S. ^{[1
]}

Reddy, B. V. Subba ^{[1
]}

Raju, A. ^{[1
]}

Ravindar, K. ^{[1
]}

Baishya, Gakul ^{[1
]}

机构：

[1] Indian Inst Chem Technol, Div Organ Chem, Hyderabad 500007, Andhra Pradesh, India

来源：

CHEMISTRY LETTERS | 2007年 / 36卷 / 12期

关键词：

D O I：

10.1246/cl.2007.1474

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Indium(III) bromide is found to catalyze efficiently the hydrothiolation of unactivated alkynes with various thiols under mild conditions to produce the corresponding dithioacetals in excellent yields. However, addition of aromatic thiols on aromatic alkynes gave the beta-vinyl sulfides in high yields. This new procedure offers significant advantages such as high conversions, short reaction times, and simplicity in operation.

引用

页码：1474 / 1475

页数：2

共 24 条

[1] Efficient and convenient synthesis of β-vinyl sulfides in nickel-catalyzed regioselective addition of thiols to terminal alkynes under solvent-free conditions [J].

Ananikov, VP ;

Orlov, NV ;

Beletskaya, IP .

ORGANOMETALLICS, 2006, 25 (08) :1970-1977

[2]

[Anonymous], 1994, SULFUR REAGENTS ORGA

[3]

Baeckvall J.-E., 1994, J ORG CHEM, V59, P5850

[4] Indium tribromide:: a highly effective catalyst for the addition of trimethylsilyl cyanide to α-hetero-substituted ketones [J].

Bandini, M ;

Cozzi, PG ;

Melchiorre, P ;

Umani-Ronchi, A .

TETRAHEDRON LETTERS, 2001, 42 (16) :3041-3043

[5] 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

[6] Rhodium(I) and iridium(I) complexes with bidentate N, N and P, N ligands as catalysts for the hydrothiolation of alkynes [J].

Burling, S ;

Field, LD ;

Messerle, BA ;

Khuong, QV ;

Turner, P .

DALTON TRANSACTIONS, 2003, (21) :4181-4191

[7] Indium tribromide-catalyzed chemoselective dithioacetalization of aldehydes in non-aqueous and aqueous media [J].

Ceschi, MA ;

Felix, LD ;

Peppe, C .

TETRAHEDRON LETTERS, 2000, 41 (50) :9695-9699

[8] Efficient and selective nickel-catalyzed addition of H-P(O) and H-S bonds to alkynes [J].

Han, LB ;

Zhang, C ;

Yazawa, H ;

Shimada, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (16) :5080-5081

[9] THE 1ST EXAMPLE OF TRANSITION-METAL-CATALYZED ADDITION OF AROMATIC THIOLS TO ACETYLENES [J].

KUNIYASU, H ;

OGAWA, A ;

SATO, KI ;

RYU, I ;

KAMBE, N ;

SONODA, N .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (14) :5902-5903

[10] Addition of benzenethiol to terminal alkynes catalyzed by hydrotris(3,5-dimethylpyrazolyl)borate-Rh(III) bis(thiolate) complex: Mechanistic studies with characterization of the key intermediate [J].

Misumi, Yoshiyuki ;

Seino, Hidetake ;

Mizobe, Yasushi .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2006, 691 (14) :3157-3164

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