Improvement in the synthesis of (Z)-organylthioenynes via hydrothiolation of buta-1,3-diynes: a comparative study using NaOH or TBAOH as base

被引：21

作者：

Santana, Amanda S. ^{[1
]}

Carvalho, Diego B. ^{[1
]}

Casemiro, Nadla S. ^{[1
]}

Hurtado, Gabriela R. ^{[1
]}

Viana, Luiz H. ^{[1
]}

Kassab, Najla M. ^{[1
]}

Barbosa, Sandro L. ^{[2
]}

Marques, Francisco A. ^{[3
]}

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

Baroni, Adriano C. M. ^{[1
]}

机构：

[1] Univ Fed Mato Grosso Sul UFMS, Ctr Ciencias Biol & Saude, LASQUIM Lab Sintese & Quim Med, BR-79070900 Campo Grande, MS, Brazil

[2] Univ Fed Vale Jequitinhonha & Mucuri, Dept Farm Bioquim, BR-39100000 Diamantina, MG, Brazil

[3] Univ Fed Parana, Dept Quim, UFPR, BR-81280340 Curitiba, PR, Brazil

[4] Univ Tecnol Fed Parana, DAQBi, Dept Quim & Biol, UTFPR, BR-80230901 Curitiba, PR, Brazil

来源：

TETRAHEDRON LETTERS | 2012年 / 53卷 / 43期

关键词：

Butanethiol (C4H9SH); Sodium hydroxide (NaOH); Tetrabutylammonium hydroxide (TBAOH); Organylthiolate anions; (Z)-Organylthioenynes; ACYL ANION EQUIVALENTS; ALKYL PHENYL SULFIDES; VINYL SULFIDES; TETRABUTYLAMMONIUM HYDROXIDE; RADICAL-ADDITION; TERMINAL ALKYNES; CATALYZED ADDITIONS; COUPLING REACTIONS; PARA-TOLUENETHIOL; CARBOXYLIC-ACIDS;

D O I：

10.1016/j.tetlet.2012.08.003

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Hydrothiolation of symmetrical and unsymmetrical buta-1,3-diynes with sodium organylthiolate anions in reflux, generated in situ by reacting C4H9SH with NaOH, afforded (Z)-organylthioenynes in low to good yields (25-80%). By using tetrabutylammonium hydroxide (TBAOH) as base instead of NaOH, the hydrothiolation of buta-1,3-diynes was more rapid and efficient, providing (Z)-organylthioenynes in good to excellent yields (70-95%). (C) 2012 Elsevier Ltd. All rights reserved.

引用

页码：5733 / 5738

页数：6

共 75 条

[1] Synthesis of (Z)-organylthioenynes using KF/Al2O3/solvent as recyclable system [J].

Alves, Diego ;

Sachini, Maraisa ;

Jacob, Raquel G. ;

Lenardao, Eder J. ;

Contreira, Maria E. ;

Savegnago, Lucielli ;

Perin, Gelson .

TETRAHEDRON LETTERS, 2011, 52 (01) :133-135

[2] Tetra-n-butylammonium hydroxide (TBAH)-catalyzed Knoevenagel condensation:: A facile synthesis of α-cyanoacrylates, α-cyanoacrylonitriles, and α-cyanoacrylamides [J].

Balalaie, S ;

Bararjanian, M .

SYNTHETIC COMMUNICATIONS, 2006, 36 (04) :533-539

[3]

Barton D.H.R., 1973, J CHEM SOC P1, P654

[4] A USEFUL METHOD FOR CONFIGURATIONAL ASSIGNMENT OF VINYL SULFIDES - STEREOCHEMICAL REASSESSMENT OF THE RADICAL-ADDITION OF BENZENETHIOL TO ALKYNES [J].

BENATI, L ;

CAPELLA, L ;

MONTEVECCHI, PC ;

SPAGNOLO, P .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1995, (08) :1035-1038

[5]

Bos M.E., 2004, ENCY REAGENTS ORGANI

[6] Rhodium-catalyzed alkyne hydrothiolation with aromatic and aliphatic thiols [J].

Cao, CS ;

Fraser, LR ;

Love, JA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (50) :17614-17615

[7] Palladium-catalyzed Sonogashira coupling reaction followed by isomerization and cyclization [J].

Cho, CS .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2005, 690 (17) :4094-4097

[8] CONVERSION OF CARBOXYLIC-ACIDS AND ESTERS INTO ACYL ANION EQUIVALENTS VIA REDUCTION LITHIATION OF THEIR KETENE PHENYLTHIOACETAL DERIVATIVES [J].

COHEN, T ;

WEISENFELD, RB .

JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (20) :3601-3603

[9] A METHOD FOR INTRODUCTION OF 2 CARBON APPENDAGES AT A CARBONYL CARBON - APPLICATION TO DOUBLE CHAIN BRANCHING AND SPIRO ANNULATION OPERATIONS [J].

COREY, EJ ;

SHULMAN, JI .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1970, 92 (18) :5522-&

[10] PHENYLTHIOMETHYLLITHIUM AND BIS(PHENYLTHIO)METHYLLITHIUM [J].

COREY, EJ ;

SEEBACH, D .

JOURNAL OF ORGANIC CHEMISTRY, 1966, 31 (12) :4097-&

← 1 2 3 4 5 6 7 8 →