Unexpectedly Easy Noncatalytic Allyl Group Transfer from Allyl Sulfides to Secondary Phosphine Sulfides

被引：0

作者：

Chernysheva, N. A. ^{[1
]}

Verkhoturova, S. I. ^{[1
]}

Nalibayeva, A. M. ^{[2
]}

Bishimbayeva, G. K. ^{[2
]}

Arbuzova, S. N. ^{[1
]}

Zinchenko, S. V. ^{[1
]}

Trofimov, B. A. ^{[1
]}

机构：

[1] Russian Acad Sci, Favorsky Irkutsk Inst Chem, Siberian Branch, Irkutsk 664033, Russia

[2] Sokolskiy Inst Fuel Catalysis & Electrochem, Alma Ata 050010, Kazakhstan

来源：

RUSSIAN JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 59卷 / 03期

关键词：

allyl sulfides; secondary phosphine sulfides; allylation; allyl(diorganyl)phosphine sulfides; PALLADIUM; ALKENES; BOND;

D O I：

10.1134/S107042802303003X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The allylation of secondary phosphine sulfides with allyl sulfides under mild catalyst-free and solvent-free conditions at 80 degrees C unexpectedly afforded allyl(diorganyl)phosphine sulfides in up to 79% yield. The products are capable of adding the initial secondary phosphine sulfides at the allyl group during the process to give the corresponding anti-Markovnikov adducts, propane-1,3-diylbis(diorganylphosphine sulfides), that are promising as extractants for heavy metals and ligands for metal-complex catalysts.

引用

页码：371 / 375

页数：5

共 19 条

[1] Celebrating 20 Years of SYNLETT - Special Essay: General Procedure for the Palladium-Catalyzed Selective Hydrophosphorylation of Alkynes [J].

Ananikov, Valentine P. ;

Khemchyan, Levon L. ;

Beletskaya, Irina P. .

SYNLETT, 2009, (15) :2375-2381

[2] Sulfur donating extractants for the separation of trivalent actinides and lanthanides [J].

Bessen, N. P. ;

Jackson, J. A. ;

Jensen, M. P. ;

Shafer, J. C. .

COORDINATION CHEMISTRY REVIEWS, 2020, 421

[3] SYNTHESIS AND ISOMERIZATION OF SEVERAL THIOALLYL ESTERS OF P(III) ACIDS [J].

DROZDOVA, YA ;

BURILOV, AR ;

PUDOVIK, MA .

RUSSIAN CHEMICAL BULLETIN, 1993, 42 (08) :1377-1379

[4] SYNTHESES OF UNSYMMETRICAL SULFIDES AND BIS(ALKYLTHIO)METHANES FROM DIPHENYLPHOSPHINODITHIOATE ESTERS [J].

GODA, K ;

HANAFUSA, F ;

INAMOTO, N .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1978, 51 (03) :818-820

[5] Organophosphorus chemistry based on elemental phosphorus: advances and horizons [J].

Gusarova, Nina K. ;

Trofimov, Boris A. .

RUSSIAN CHEMICAL REVIEWS, 2020, 89 (02) :225-249

[6] Catalyst- and Solvent-Free Addition of the P-H Species to Alkenes and Alkynes: A Green Methodology for C-P Bond Formation [J].

Gusarova, Nina K. ;

Chernysheva, Nataliya A. ;

Trofimov, Boris A. .

SYNTHESIS-STUTTGART, 2017, 49 (21) :4783-4807

[7]

Kamer P.C., 2012, PHOSPHORUS 3 LIGANDS

[8]

Kosolapoff G.M., 1972, ORGANIC PHOSPHORUS C, V4, P40

[9] Recent advances in the use of phosphorus-centered radicals in organic chemistry [J].

Leca, D ;

Fensterbank, L ;

Lacôte, E ;

Malacria, M .

CHEMICAL SOCIETY REVIEWS, 2005, 34 (10) :858-865

[10] Facile Non-Catalyzed Synthesis of Tertiary Phosphine Sulfides by Regioselective Addition of Secondary Phosphine Sulfides to Alkenes [J].

Malysheva, Svetlana F. ;

Gusarova, Nina K. ;

Artem'ev, Alexander V. ;

Belogorlova, Nataliya A. ;

Albanov, Alexander I. ;

Borodina, Tatyana N. ;

Smirnov, Vladimir I. ;

Trofimov, Boris A. .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (12) :2516-2521

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