Practical synthesis of unsymmetrical disulfides promoted by bromodimethylsulfonium bromide

被引：5

作者：

Dong, Bo ^{[1
]}

Chen, Yifeng ^{[1
]}

Xie, Shubing ^{[3
]}

Zhang, Jieying ^{[1
]}

Shen, Jian ^{[1
,2
]}

Xie, Lan-Gui ^{[1
]}

机构：

[1] Nanjing Normal Univ, Natl & Local Joint Engn Res Ctr Biomed Funct Mat, Sch Chem & Mat Sci, Nanjing 210023, Peoples R China

[2] Nanjing Univ, Jiangsu Engn Res Ctr Interfacial Chem, Nanjing 210023, Peoples R China

[3] Anhui Changjiang Inst Metrol, Hefei 230088, Peoples R China

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2023年 / 21卷 / 05期

基金：

中国国家自然科学基金;

关键词：

EFFICIENT SYNTHESIS; DISULFANES; PRECURSORS; ALKENES; THIOLS; BONDS;

D O I：

10.1039/d2ob02124b

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Oxidative cross-coupling of two thiols is the most direct tool for the synthesis of unsymmetrical disulfides and highly desirable across academia and industry. However, the inevitable formation of significant amounts of the corresponding symmetrical by-products is a major issue. We herein present a method toward the synthesis of unsymmetrical disulfides in which the homo-coupling of the thiols is effectively inhibited by adding the two thiols sequentially, taking advantage of rapid oxidation of the thiol by bromodimethylsulfonium bromide.

引用

页码：930 / 934

页数：5

共 50 条

[31] Directed oxidative coupling of thiols in the synthesis of unsymmetrical disulfides
D. A. Burmistrova
I. V. Smolyaninov
N. T. Berberova
Russian Chemical Bulletin, 2020, 69 : 990 - 995
[32] An efficient and convenient synthesis of unsymmetrical disulfides from thioacetates
Lach, Slawomir
Demkowicz, Sebastian
Witt, Dariusz
TETRAHEDRON LETTERS, 2013, 54 (51) : 7021 - 7023
[33] Directed oxidative coupling of thiols in the synthesis of unsymmetrical disulfides
Burmistrova, D. A.
Smolyaninov, I., V
Berberova, N. T.
RUSSIAN CHEMICAL BULLETIN, 2020, 69 (05) : 990 - 995
[34] Recent Developments in the Synthesis of Unsymmetrical Disulfanes (Disulfides). A Review
Musiejuk, Mateusz
Witt, Dariusz
ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 2015, 47 (02) : 95 - 131
[35] SYNTHESIS OF UNSYMMETRICAL DISULFIDES WITH THIOLSULFONATES IMMOBILIZED ON A POLYSTYRENE SUPPORT
RAJCA, A
WIESSLER, M
TETRAHEDRON LETTERS, 1990, 31 (42) : 6075 - 6076
[36] NEW SYNTHESIS OF UNSYMMETRICAL DISULFIDES - PRELIMINARY-REPORT
DUBS, P
STUSSI, R
HELVETICA CHIMICA ACTA, 1976, 59 (04) : 1307 - 1311
[37] An Overview of Recent Advances in the Synthesis of Organic Unsymmetrical Disulfides
Ong, Chiu Ling
Titinchi, Salam
Juan, Joon Ching
Khaligh, Nader Ghaffari
HELVETICA CHIMICA ACTA, 2021, 104 (08)
[38] GRIGNARD-REAGENT FACILITATED SYNTHESIS OF UNSYMMETRICAL DISULFIDES
MUNAVALLI, S
ROSSMAN, DI
ROHRBAUGH, DK
FERGUSON, CP
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1991, 201 : 53 - ORGN
[39] Efficient and practical synthesis of unsymmetrical disulfides via base-catalyzed aerobic oxidative dehydrogenative coupling of thiols
Qiu, Xu
Yang, Xiaoxue
Zhang, Yiqun
Song, Song
Jiao, Ning
ORGANIC CHEMISTRY FRONTIERS, 2019, 6 (13) : 2220 - 2225
[40] SILICON IN ORGANOSULFUR CHEMISTRY .2. SYNTHESIS OF UNSYMMETRICAL DISULFIDES
CAPOZZI, G
CAPPERUCCI, A
DEGL'INNOCENTI, A
DELDUCE, R
MENICHETTI, S
TETRAHEDRON LETTERS, 1989, 30 (22) : 2995 - 2998

← 1 2 3 4 5 →