Nickel-catalyzed addition of benzenethiol to alkynes: Formation of carbon-sulfur and carbon-carbon bonds

被引：24

作者：

Ananikov, V. P.

Zalesskiy, S. S.

Orlov, N. V.

Beletskaya, I. P.

机构：

[1] Russian Acad Sci, ND Zelinskii Organ Chem Inst, Moscow 119991, Russia

[2] Moscow MV Lomonosov State Univ, Moscow 119992, Russia

来源：

RUSSIAN CHEMICAL BULLETIN | 2006年 / 55卷 / 11期

基金：

俄罗斯基础研究基金会;

关键词：

nickel complexes; transition metal catalysis; alkynes; alkenyl sulfides; dienyl sulfides; green chemistry;

D O I：

10.1007/s11172-006-0557-8

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Nickel-catalyzed addition of benzenethiol to alkynes leads to alkenyl and dienyl sulfides; the direction of the process can be controlled by varying the PhSH/alkyne ratio. An advanced procedure, which ensures higher yields of 2-phenylsulfanylalkenes, includes gradual addition of alkyne to the other reactants. The structures of conjugated dienyl sulfides formed in the reaction were determined by 2D NMR spectroscopy.

引用

收藏

页码：2109 / 2113

页数：5

相关论文

共 22 条

[1]

AKOPYAN LA, 1973, ZH ORG KHIM+, V9, P2004

[2] Transition-metal-catalyzed addition of heteroatom-hydrogen bonds to alkynes [J].

Alonso, F ;

Beletskaya, IP ;

Yus, M .

CHEMICAL REVIEWS, 2004, 104 (06) :3079-3159

[3] 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

[4] Nickel(II) chloride-catalyzed regioselective hydrothiolation of alkynes [J].

Ananikov, VP ;

Malyshev, DA ;

Beletskaya, IP ;

Aleksandrov, GG ;

Eremenko, IL .

ADVANCED SYNTHESIS & CATALYSIS, 2005, 347 (15) :1993-2001

[5] Mechanistic study of palladium catalyzed S-S and Se-Se bonds addition to alkynes [J].

Ananikov, VP ;

Kabeshov, MA ;

Beletskaya, IP ;

Aleksandrov, GG ;

Eremenko, IL .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2003, 687 (02) :451-461

[6] FREE-RADICAL ADDITIONS OF DISELENIDES TO DIMETHYL ACETYLENEDICARBOXYLATE, METHYL PROPIOLATE, AND DIMETHYL MALEATE [J].

BACK, TG ;

KRISHNA, MV .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (11) :2533-2536

[7] Catalytic Markovnikov and anti-Markovnikov functionalization of alkenes and alkynes: Recent developments and trends [J].

Beller, M ;

Seayad, J ;

Tillack, A ;

Jiao, H .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (26) :3368-3398

[8]

BICEV P, 1973, GAZZ CHIM ITAL, V103, P849

[9] CYCLISATION OF 2-METHYLBUT-3-YN-2-OL .I. CYCLISATION TO AROMATIC COMPOUNDS [J].

CHINI, P ;

SANTAMBROGIO, A ;

PALLADINO, N .

JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1967, (09) :830-+

[10]

CHUKHADZHYAN GA, 1972, ZH ORG KHIM, V8, P2004