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

[41] Efficient one-pot synthesis of unsymmetrical cysteine disulfides
Hunter, Roger
Stellenboom, Nashia
Caira, Mino R.
SYNLETT, 2008, (02) : 252 - 254
[42] Synthesis of unsymmetrical disulfides via the cross-dehydrogenation of thiols
Ren, Shangfeng
Luo, Nianhua
Liu, Kunming
Liu, Jin-Biao
JOURNAL OF CHEMICAL RESEARCH, 2021, 45 (5-6) : 365 - 373
[43] A NEW MILD SYNTHESIS OF UNSYMMETRICAL DISULFIDES BY REACTION OF DITHIOPEROXYESTERS WITH THIOLS
LERIVEREND, C
METZNER, P
SYNTHESIS-STUTTGART, 1994, (08): : 761 - 762
[44] CHEMISTRY OF ALIPHATIC DISULFIDES .11. SYNTHESIS OF UNSYMMETRICAL BISDISULFIDES
HISKEY, RG
HARPP, DN
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1965, 87 (17) : 3965 - &
[45] Direct Synthesis of Unsymmetrical Glycosyl Disulfides from Glycosyl Bromides
Kundu, Monalisa
Misra, Anup Kumar
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 2021 (26) : 3759 - 3767
[46] Facile methylthiomethylation of the carboxylic acid with bromodimethylsulfonium bromide
Dong, Bo
Huang, Yunze
Zhang, Xing
Shen, Jian
Xie, Lan-Gui
GREEN SYNTHESIS AND CATALYSIS, 2022, 3 (03): : 278 - 281
[47] A practical and general synthesis of unsymmetrical terphenyls
Antelo Miguez, Jose M.
Angel Adrio, Luis
Sousa-Pedrares, Antonio
Vila, Jose M.
Hii, King Kuok
JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (20): : 7771 - 7774
[48] Practical synthesis of unsymmetrical polyamine amides
Blagbrough, IS
Geall, AJ
TETRAHEDRON LETTERS, 1998, 39 (5-6) : 439 - 442
[49] CONFORMATION OF UNSYMMETRICAL DIARYL DISULFIDES
SOROKINA, LA
VULFSON, SG
KATAEVA, LM
VERESHCHAGIN, AN
KATAEV, EG
VINOKUROVA, RI
BULLETIN OF THE ACADEMY OF SCIENCES OF THE USSR DIVISION OF CHEMICAL SCIENCE, 1977, 26 (10): : 2205 - 2207
[50] A CONVENIENT SYNTHESIS OF NOVEL UNSYMMETRICAL ACYL THIOACYL DISULFIDES AND ACYL O,O-DIALKYLTHIOPHOSPHORYL DISULFIDES
KATO, S
WATARAI, H
KATADA, T
MIZUTA, M
MIYAGAWA, K
ISHIDA, M
SYNTHESIS-STUTTGART, 1981, (05): : 370 - 371

← 1 2 3 4 5 →