Directed oxidative coupling of thiols in the synthesis of unsymmetrical disulfides

被引：10

作者：

Burmistrova, D. A. ^{[1
]}

Smolyaninov, I., V ^{[1
,2
]}

Berberova, N. T. ^{[1
]}

机构：

[1] Astrakhan State Tech Univ, 16 Ul Tatishcheva, Astrakhan 414056, Russia

[2] Russian Acad Sci, Southern Sci Ctr, Fed Res Ctr, 41 Prosp Chekhova, Rostov Na Donu 344006, Russia

来源：

RUSSIAN CHEMICAL BULLETIN | 2020年 / 69卷 / 05期

基金：

俄罗斯基础研究基金会;

关键词：

disulfides; thiols; oxidative coupling; o-benzoquinones; o-iminobenzoquinones; N-methylpyrrolidone; HYDROGEN-SULFIDE; ELECTROCHEMICAL TRANSFORMATIONS; ANTI/PROOXIDANT ACTIVITY; ANTIRADICAL ACTIVITY; RADICAL-CATION; FUNCTIONALIZATION; PRODUCTS;

D O I：

10.1007/s11172-020-2860-1

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Oxidative coupling of two different thiols bearing aliphatic, alicyclic, aromatic, and hetero-aromatic moieties promoted by mild oxidizing agents,viz., sterically hinderedo-benzo(imino)-quinones, carried out inN-methylpyrrolidone at room temperature led to unsymmetrical disulfides. Among the studied oxidizers, the most active was 3,6-di-tert-butyl-o-benzoquinone, which, in contrast to 3,5-di-tert-butyl-o-benzoquinone, was not involved in the Michael addition. Under the optimal reaction conditions, the yields of the target unsymmetrical disulfides reach 81%.

引用

页码：990 / 995

页数：6

共 50 条

[1] Directed oxidative coupling of thiols in the synthesis of unsymmetrical disulfides
D. A. Burmistrova
I. V. Smolyaninov
N. T. Berberova
[J]. Russian Chemical Bulletin, 2020, 69 : 990 - 995
[2] 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
[J]. ORGANIC CHEMISTRY FRONTIERS, 2019, 6 (13) : 2220 - 2225
[3] Ground solid permanganate oxidative coupling of thiols into symmetrical/unsymmetrical disulfides: selective and improved process
Nguyen, Ngan-Giang Thi
Nguyen, Xuan-Triet
Nguyen, Ngoc-Huy
Luu, Thi Xuan Thi
Dao, Xuan-Tien
[J]. JOURNAL OF SULFUR CHEMISTRY, 2022, 43 (06) : 593 - 605
[4] Oxidative coupling of thiols to disulfides by piperazinium dichromate
Movassagh, B
Lakouraj, MM
Ghodrati, K
[J]. INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 2002, 41 (06): : 1293 - 1295
[5] Synthesis of disulfides by laccase-catalyzed oxidative coupling of heterocyclic thiols
Abdel-Mohsen, Heba T.
Sudheendran, Kavitha
Conrad, Juergen
Beifuss, Uwe
[J]. GREEN CHEMISTRY, 2013, 15 (06) : 1490 - 1495
[6] Synthesis of disulfides by the oxidative coupling of thiols with calcium hypochlorite and silica gel in hexane
Hirano, M
Yakabe, S
Uraoka, N
Morimoto, T
[J]. ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 1998, 30 (03) : 360 - 363
[7] BAKER YEAST CATALYZED OXIDATIVE COUPLING OF THIOLS TO DISULFIDES
RAO, KR
KUMAR, HMS
[J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1991, 1 (10) : 507 - 508
[8] Oxidative coupling of thiols to disulfides with iodine in wet acetonitrile
Zeynizadeh, B
[J]. JOURNAL OF CHEMICAL RESEARCH, 2002, (11) : 564 - 566
[9] Synthesis of unsymmetrical disulfides via the cross-dehydrogenation of thiols
Ren, Shangfeng
Luo, Nianhua
Liu, Kunming
Liu, Jin-Biao
[J]. JOURNAL OF CHEMICAL RESEARCH, 2021, 45 (5-6) : 365 - 373
[10] A NEW MILD SYNTHESIS OF UNSYMMETRICAL DISULFIDES BY REACTION OF DITHIOPEROXYESTERS WITH THIOLS
LERIVEREND, C
METZNER, P
[J]. SYNTHESIS-STUTTGART, 1994, (08): : 761 - 762

← 1 2 3 4 5 →