Palladium-catalyzed synthesis of vinyl phosphines from ketones

被引：40

作者：

Gilbertson, SR ^{[1
]}

Fu, Z ^{[1
]}

Starkey, GW ^{[1
]}

机构：

[1] Washington Univ, Dept Chem, St Louis, MO 63130 USA

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 49期

关键词：

catalysis; coupling reactions; palladium; phosphines;

D O I：

10.1016/S0040-4039(99)01819-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The palladium-catalyzed conversion of vinyl triflates to vinyl phosphines is reported. This process allows for the synthesis of vinyl phosphines from ketones. Selective enolization of a variety of ketones followed by trapping of the enolate as the vinyl triflate is reported. The vinyl triflates are then converted to the corresponding vinyl phosphine through palladium catalysis. The resulting vinyl phosphines can then be reduced to give alkyl phosphines. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

收藏

页码：8509 / 8512

页数：4

相关论文

共 18 条

[1]

BRUNNER H, 1991, B SOC CHIM BELG, V100, P247

[2] SYNTHESIS OF CHIRAL 2,2'-BIS(DIPHENYLPHOSPHINO)-1,1'-BINAPHTHYL (BINAP) VIA A NOVEL NICKEL-CATALYZED PHOSPHINE INSERTION [J].

CAI, DW ;

PAYACK, JF ;

BENDER, DR ;

HUGHES, DL ;

VERHOEVEN, TR ;

REIDER, PJ .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (23) :7180-7181

[3] A modular approach to ligands for asymmetric pi-allyl palladium catalysed additions [J].

Gilbertson, SR ;

Chang, CWT .

CHEMICAL COMMUNICATIONS, 1997, (10) :975-976

[4] Palladium-catalyzed synthesis of phosphine-containing amino acids [J].

Gilbertson, SR ;

Starkey, GW .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (09) :2922-2923

[5] Synthesis of (dicyclohexylphosphino)serine, its incorporation into a dodecapeptide, and the coordination of rhodium [J].

Gilbertson, SR ;

Wang, XF .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (02) :434-435

[6] VERSATILE BUILDING-BLOCK FOR THE SYNTHESIS OF PHOSPHINE-CONTAINING PEPTIDES - THE SULFIDE OF DIPHENYLPHOSPHINOSERINE [J].

GILBERTSON, SR ;

CHEN, GH ;

MCLOUGHLIN, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (10) :4481-4482

[7] The combinatorial synthesis of chiral phosphine ligands [J].

Gilbertson, SR ;

Wang, XF .

TETRAHEDRON LETTERS, 1996, 37 (36) :6475-6478

[8] Synthesis of phosphine-rhodium complexes attached to a standard peptide synthesis resin [J].

Gilbertson, SR ;

Wang, XF ;

Hoge, GS ;

Klug, CA ;

Schaefer, J .

ORGANOMETALLICS, 1996, 15 (22) :4678-4680

[9] RAPID AND MILD DEOXYGENATION OF ORGANOHETEROATOM OXIDES WITH THE EFFICIENT ELECTRON-TRANSFER SYSTEM SMI2 TETRAHYDROFURAN HEXAMETHYLPHOSPHORIC TRIAMIDE [J].

HANDA, Y ;

INANAGA, J ;

YAMAGUCHI, M .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (05) :298-299

[10] Synthesis of vinyldiphenylphosphines by Pd-catalyzed cross-coupling reactions of diphenylphosphine with alkenylhalides. [J].

Kazankova, MA ;

Chirkov, EA ;

Kochetkov, AN ;

Efimova, IV ;

Beletskaya, IP .

TETRAHEDRON LETTERS, 1999, 40 (03) :573-576