A new odorless one-pot synthesis of thioesters and selenoesters promoted by Rongalite®

被引：49

作者：

Dan, Weixing ^{[1
]}

Deng, Hongjuan ^{[1
]}

Chen, Jiuxi ^{[1
]}

Liu, Miaochang ^{[1
]}

Ding, Jinchang ^{[1
,2
]}

Wu, Huayue ^{[1
]}

机构：

[1] Wenzhou Univ, Coll Chem & Mat Engn, Wenzhou 325035, Peoples R China

[2] Wenzhou Vocat & Tech Coll, Wenzhou 325035, Peoples R China

来源：

TETRAHEDRON | 2010年 / 66卷 / 37期

关键词：

Rongalite (R); Acylation; Disulfides; Anhydrides; Thioesters; Selenoesters; UNSYMMETRICAL DIORGANYL SELENIDES; S-S BOND; EFFICIENT SYNTHESIS; THIOL ESTERS; DIPHENYL DISELENIDE; CONVENIENT PREPARATION; SELENOL ESTERS; ACID-CHLORIDES; ACYL RADICALS; ALKYL-HALIDES;

D O I：

10.1016/j.tet.2010.07.023

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Rongalite (R) promotes cleavage of diaryl disulfides generating chalcogenolate anions that then undergo facile acylation with anhydrides in the presence of CsF to afford thioesters (3) with good to excellent yields. By using the present protocol, 5-arylthio-5-oxopentanoic acid (4) can be facilely prepared. The important features of the methodology are broad substrate scope, simple operation, and no requirement for metal catalysts. It is noteworthy that acylations of diphenyl diselane with anhydrides are also conducted smoothly to afford selenoesters (5) in good yields under the standard conditions. (C) 2010 Elsevier Ltd. All rights reserved.

引用

页码：7384 / 7388

页数：5

共 64 条

[1] trans-1,3-dithiane-1,3-dioxide; a chiral acyl anion equivalent. Enantioselective synthesis of alpha-hydroxy- carboxylic acids, esters, amides and ketones
Aggarwal, VK
Thomas, A
Schade, S
[J]. TETRAHEDRON, 1997, 53 (48) : 16213 - 16228
[2] Rhodium-catalyzed reductive coupling of disulfides and diselenides with alkyl halides, using hydrogen as a reducing agent
Ajiki, K
Hirano, M
Tanaka, K
[J]. ORGANIC LETTERS, 2005, 7 (19) : 4193 - 4195
[3] Rhodium-catalyzed alkylthio exchange reaction of thioester and disulfide
Arisawa, Mieko
Kubota, Tomohiro
Yamaguchi, Masahiko
[J]. TETRAHEDRON LETTERS, 2008, 49 (12) : 1975 - 1978
[4] OXIDATION OF HYDRAZINES WITH BENZENESELENINIC ACID AND ANHYDRIDE
BACK, TG
COLLINS, S
KERR, RG
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (08) : 1564 - 1570
[5] Balzani V, 2000, ANGEW CHEM INT EDIT, V39, P3348, DOI 10.1002/1521-3773(20001002)39:19<3348::AID-ANIE3348>3.0.CO
[6] 2-X
[7] Convenient and Efficient Synthesis of Thiol Esters using Zinc Oxide as a Heterogeneous and Eco-Friendly Catalyst
Bandgar, Babasaheb Pandurang
More, Parmeshwar Eknath
Kamble, Vinod Tribhuvannathji
Sawant, Sanjay Suresh
[J]. AUSTRALIAN JOURNAL OF CHEMISTRY, 2008, 61 (12) : 1006 - 1010
[8] Dess-Martin periodinane mediated synthesis of thioesters from aldehydes
Bandgar, Sunita B.
Bandgar, B. P.
Korbad, B. L.
Sawant, S. S.
[J]. TETRAHEDRON LETTERS, 2007, 48 (07) : 1287 - 1290
[9] 6 MEMBERED RING-OPENING OF ISOPROPYLIDENE MALONATE DERIVATIVES - SYNTHESIS OF ALPHA,BETA-UNSATURATED THIOARYL AND SELENOARYL CARBOXYLIC ESTERS
BAO, WL
ZHANG, YM
[J]. SYNTHETIC COMMUNICATIONS, 1995, 25 (02) : 143 - 148
[10] Tributylstannyl aryl selenides as efficient arylselenating agents in the synthesis of seleno esters
Beletskaya, IP
Sigeev, AS
Peregudov, AS
Petrovskii, PV
[J]. RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2001, 37 (12) : 1703 - 1709

← 1 2 3 4 5 6 7 →