One-pot synthesis of mixed (Z)-1,2-bis(organylchalcogene)-1-alkenes precursors of the novel β-organylthio vinyllithium intermediates

被引：5

作者：

Dabdoub, Miguel J. ^{[1
]}

Dabdoub, Vania B. ^{[1
]}

Pereira, Marco A. ^{[1
]}

Baroni, Adriano C. M. ^{[2
]}

Marques, Francisco A. ^{[3
]}

de Oliveira, Paulo R. ^{[4
]}

Guerrero, Palimecio G., Jr. ^{[4
]}

机构：

[1] Univ Sao Paulo, Lab Compostos Organocalcogenios, Ribeirao Preto, SP, Brazil

[2] Univ Fed Mato Grosso do Sul, UFMS, Dept Farm Bioquim, Campo Grande, MS, Brazil

[3] Univ Fed Parana, UFPR, Dept Quim, BR-80060000 Curitiba, Parana, Brazil

[4] Univ Tecnol Fed Parana, UTFPR, Lab Sintese Organ & Produtos Nat, Dept Quim & Biol, Curitiba, Parana, Brazil

来源：

TETRAHEDRON LETTERS | 2010年 / 51卷 / 39期

关键词：

Hydrochalcogenation; Transmetallation; Thioacetylenes; beta-Organylthio vinyllithium; STEREOSELECTIVE-SYNTHESIS; VINYLIC TELLURIDES; REGIOSELECTIVE-SYNTHESIS; VERSATILE GENERATION; TE/LI EXCHANGE; HIGHLY REGIO; HYDROZIRCONATION; HYDROALUMINATION; SELENIDES; SULFIDES;

D O I：

10.1016/j.tetlet.2010.07.112

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

One-pot hydrochalcogenation of 1-phenylthioacetylenes using organylselenolate and organyltellurolate anions generated by the insertions of selenium and tellurium in n-organyl lithium produced (Z)-1,2-bis(organylchalcogene)-1-alkenes. The chemical reactivity of these mixed 1,2-bis(organylchalcogene)-1-alkenes was studied by Te/Li and Se/Li stereoretentive exchanges carried out with n-butyl lithium, furnishing the new intermediate species (Z)-beta-organylthio vinyllithium anions, which were trapped with aldehydes, to give the (Z)-3-hydroxy vinyl thioethers with total control of the regio- and stereochemistry. (c) 2010 Elsevier Ltd. All rights reserved.

引用

页码：5141 / 5145

页数：5

共 60 条

[11] Synthesis of (Z)-1-Organylthiobut-1-en-3-ynes: Hydrothiolation of Symmetrical and Unsymmetrical Buta-1,3-diynes [J].

Dabdoub, Miguel J. ;

Dabdoub, Vania B. ;

Lenardao, Eder J. ;

Hurtado, Gabriela R. ;

Barbosa, Sandro L. ;

Guerrero, Palimecio G., Jr. ;

Nazario, Carlos E. D. ;

Viana, Luiz H. ;

Santana, Amanda S. ;

Baroni, Adriano C. M. .

SYNLETT, 2009, (06) :986-990

[12] Hydrozirconation of acetylenic chalcogenides. Synthesis and reactions of zirconated vinyl chalcogenide intermediates [J].

Dabdoub, MJ ;

Begnini, ML ;

Guerrero, PG .

TETRAHEDRON, 1998, 54 (11) :2371-2400

[13] Hydroalumination of phenylthioacetylenes.: Synthesis and reactions of (Z)- and (E)-1-butyltelluro-1-phenylthio-1-alkenes [J].

Dabdoub, MJ ;

Guerrero, PG .

TETRAHEDRON LETTERS, 2001, 42 (41) :7167-7172

[14] Synthesis of (Z)-1-phenylseleno-1,4-diorganyl-1-buten-3-ynes:: hydroselenation of symmetrical and unsymmetrical 1,4-diorganyl-1,3-butadiynes [J].

Dabdoub, MJ ;

Baroni, ACM ;

Lenardâo, EJ ;

Gianeti, TR ;

Hurtado, GR .

TETRAHEDRON, 2001, 57 (20) :4271-4276

[15] Hydrochalcogenation of phenylthioacetylenes.: Synthesis of mixed (Z)-trisubstituted 1,2-bis(organylchalcogeno)-1-alkenes [J].

Dabdoub, MJ ;

Dabdoub, VB ;

Pereira, MA .

TETRAHEDRON LETTERS, 2001, 42 (09) :1595-1597

[16] SYNTHESIS OF (E)-VINYLIC TELLURIDES AND THEIR TRANSFORMATION INTO ALPHA,BETA-UNSATURATED ESTERS AND CARBOXYLIC-ACIDS [J].

DABDOUB, MJ ;

BEGNINI, ML ;

CASSOL, TM ;

GUERRERO, PG ;

SILVEIRA, CC .

TETRAHEDRON LETTERS, 1995, 36 (42) :7623-7626

[17] SYNTHESIS OF VINYLIC TELLURIDES [J].

DABDOUB, MJ ;

DABDOUB, VB ;

COMASSETO, JV ;

PETRAGNANI, N .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1986, 308 (02) :211-222

[18] Hydrozirconation of lithium alkynylselenolate anions.: Generation and reactions of α-zirconated vinyl selenide intermediates [J].

Dabdoub, MJ ;

Begnini, ML ;

Guerrero, PG ;

Baroni, ACM .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (01) :61-67

[19] (1Z,3Z)-buta-1,3-dienyl-1-lithium species and substituted tellurophenes by Te/Li exchange on (1Z,3Z)-butyltelluro-1,3-butadienes and (1Z,3Z)-1,4-bis(butyltelluro)-1,3-butadienes. [J].

Dabdoub, MJ ;

Dabdoub, VB ;

Guerrero, PG ;

Silveira, CC .

TETRAHEDRON, 1997, 53 (12) :4199-4218

[20] HIGHLY CHEMOSELECTIVE TRIPLE BOND REDUCTIONS ON UNSYMMETRICAL 1,4-DIORGANYL-1,3-BUTADIYNES [J].

DABDOUB, MJ ;

DABDOUB, VB .

TETRAHEDRON, 1995, 51 (36) :9839-9850

← 1 2 3 4 5 6 →