Solvent-free palladium-catalyzed addition of diaryl dichalcogenides to alkynes

被引：20

作者：

Ananikov, VP

Beletskaya, IP

机构：

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

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

来源：

RUSSIAN CHEMICAL BULLETIN | 2004年 / 53卷 / 03期

关键词：

vinyl sulfides; vinyl selenides; stereoselective addition; solvent-free reaction; homogeneous catalysis; palladium complexes;

D O I：

10.1023/B:RUCB.0000035637.57608.51

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Solvent-free palladium-catalyzed addition of diaryl disulfides and diselenides to terminal alkynes makes it possible to achieve high stereoselectivity and almost 100% yields in approximate to10 min using only 0.1 mol.% catalyst. Both Pd(PPh3)(4) and easily available Pd(OAc)(2) and PdCl2 can be used in the reaction with an excess of triphenylphosphine. The catalyst and triphenylphosphine are readily recycled for repeated use. The study of the mechanism of the solvent-free catalytic reaction indicates that the process involves binuclear palladium complexes.

引用

收藏

页码：561 / 565

页数：5

相关论文

共 26 条

[1] Palladium-catalyzed addition of disulfides and diselenides to alkynes under solvent free conditions [J].

Ananikov, VP ;

Beletskaya, IP .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2004, 2 (03) :284-287

[2] 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

[3] New approach to stereochemical structure determination of bis-selenium-subsituted alkenes [J].

Ananikov, VP ;

Beletskaya, IP .

RUSSIAN CHEMICAL BULLETIN, 2003, 52 (04) :811-816

[4] Mechanistic investigation and new catalyst design in palladium- and platinum-catalyzed Se-Se bond addition to alkynes [J].

Ananikov, VP ;

Beletskaya, IP ;

Aleksandrov, GG ;

Eremenko, IL .

ORGANOMETALLICS, 2003, 22 (07) :1414-1421

[5] Palladium-catalysed amination of halopyridines on a KF-alumina surface [J].

Basu, B ;

Jha, S ;

Mridha, NK ;

Bhuiyan, MMH .

TETRAHEDRON LETTERS, 2002, 43 (44) :7967-7969

[6] Synthesis and characterization of benzylselenolate complexes of palladium(II) and platinum(II) [J].

Dey, S ;

Jain, VK ;

Varghese, B .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2001, 623 (1-2) :48-55

[7] Microwave irradiation in solvent-free conditions:: an eco-friendly methodology to prepare indazoles, pyrazolopyridines and bipyrazoles by cycloaddition reactions [J].

Díaz-Ortiz, A ;

de la Hoz, A ;

Langa, F .

GREEN CHEMISTRY, 2000, 2 (04) :165-172

[8] Microwave chemistry [J].

Galema, SA .

CHEMICAL SOCIETY REVIEWS, 1997, 26 (03) :233-238

[9] Formation and structural characterization of novel polynuclear palladium selenolato complexes [Pd3Se(SePh)3(PPh3)3]Cl and [Pd6Cl2Se4(SePh)2(PPh3)6] [J].

Hannu-Kuure, MS ;

Palda'n, K ;

Oilunkaniemi, R ;

Laitinen, RS ;

Ahlgrén, M .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2003, 687 (02) :538-544

[10] Solventless Suzuki coupling reactions on palladium-doped potassium fluoride alumina [J].

Kabalka, GW ;

Wang, L ;

Pagni, RM ;

Hair, CM ;

Namboodiri, V .

SYNTHESIS-STUTTGART, 2003, (02) :217-222