The use of phosphine ligands to control the regiochemistry of Pd-catalyzed hydrostannations of 1-alkynes:: Synthesis of (E)-1-tributylstannyl-1-alkenes

被引：72

作者：

Darwish, Alla ^{[1
]}

Lang, Adam ^{[1
]}

Kim, Thomas ^{[1
]}

Chong, J. Michael ^{[1
]}

机构：

[1] Univ Waterloo, Dept Chem, Guelph Waterloo Program Grad Work Chem & Biochem, Waterloo, ON N2L 3G1, Canada

来源：

ORGANIC LETTERS | 2008年 / 10卷 / 05期

关键词：

D O I：

10.1021/ol702982x

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The regiochemistry of palladium-catalyzed hydrostannations of terminal alkynes is dramatically influenced by ligand effects. Use of phosphines such as Cy(3)P, t-Bu(2)PCH(2)t-Bu, and t-Bu(3)P provides (E)-1-tributylstannyl-1-alkenes with regioselectivities up to > 99:< 1 for substrates where the commonly used Ph(3)P shows much lower regioselectivities.

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收藏

页码：861 / 864

页数：4

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共 30 条

[1] Identification of female sex pheromone of the legume pod borer, Maruca vitrata and antagonistic effects of geometrical isomers [J].

Adati, T ;

Tatsuki, S .

JOURNAL OF CHEMICAL ECOLOGY, 1999, 25 (01) :105-115

[2] Palladium-catalysed hydrostannylations of 1-bromoalkynes. A practical synthesis of (E)-1-stannylalk-1-enes [J].

Boden, CDJ ;

Pattenden, G ;

Ye, T .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1996, (20) :2417-2419

[3] COMPONENTS OF FEMALE SEX-PHEROMONE OF SPOTTED BOLLWORM, EARIAS-VITTELLA F (LEPIDOPTERA, NOCTUIDAE) - IDENTIFICATION AND FIELD-EVALUATION IN PAKISTAN [J].

CORK, A ;

CHAMBERLAIN, DJ ;

BEEVOR, PS ;

HALL, DR ;

NESBITT, BF ;

CAMPION, DG ;

ATTIQUE, MR .

JOURNAL OF CHEMICAL ECOLOGY, 1988, 14 (03) :929-945

[4] The hydrostannation of a propargylglycine derivative [J].

Crisp, GT ;

Gebauer, MG .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1997, 532 (1-2) :83-88

[5] Stereoselective hydrostannation of substituted alkynes with trineophyltin hydride [J].

Dodero, VI ;

Koll, LC ;

Mandolesi, SD ;

Podestá, JC .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2002, 650 (1-2) :173-180

[6] A straightforward approach towards piperidines via Stille coupling and subsequent 1,4-addition of amines [J].

Dörrenbächer, S ;

Kazmaier, U ;

Ruf, S .

SYNLETT, 2006, (04) :547-550

[7] Convergent stereocontrolled synthesis of substituted exo-glycals by Stille cross-coupling of halo-exo-glycals and stannanes [J].

Gomez, Ana M. ;

Barrio, Aitor ;

Amurrio, Inigo ;

Valverde, Serafin ;

Jarosz, Slawomir ;

Lopez, J. Cristobal .

TETRAHEDRON LETTERS, 2006, 47 (35) :6243-6246

[8] DICHLOROBIS(TRICYCLOHEXYLPHOSPHINE)PALLADIUM(II) - SYNTHESIS AND CRYSTAL-STRUCTURE - AN EXCEPTIONALLY SIMPLE AND EFFICIENT PREPARATION OF BIS(TRICYCLOHEXYLPHOSPHINE)PALLADIUM(0) [J].

GRUSHIN, VV ;

BENSIMON, C ;

ALPER, H .

INORGANIC CHEMISTRY, 1994, 33 (21) :4804-4806

[9] Cuprous chloride accelerated Stille reactions. A general and effective coupling system for sterically congested substrates and for enantioselective synthesis [J].

Han, XJ ;

Stoltz, BM ;

Corey, EJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (33) :7600-7605

[10] Rapid methylation on carbon frame works for pet tracer synthesis: Part 7.: Rapid methylation on carbon frameworks useful for the synthesis of 11C H3-incorporated PET tracers:: Pd(0)-mediated rapid coupling of methyl iodide with an alkenyltributylstannane leading to a 1-methylalkenetl [J].

Hosoya, T ;

Sumi, K ;

Doi, H ;

Wakao, M ;

Suzuki, M .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2006, 4 (03) :410-415