Aerobic oxidation of thiols to disulfides under ball-milling in the absence of any catalyst, solvent, or base

被引:31
作者
Chatterjee, Tanmay [1 ]
Ranu, Brindaban C. [1 ]
机构
[1] Indian Assoc Cultivat Sci, Dept Organ Chem, Kolkata 700032, India
关键词
(S)-PROLINE-CONTAINING DIPEPTIDES; EFFICIENT SYNTHESIS; DIPHENYL DISULFIDE; TERMINAL ALKYNES; DERIVATIVES; OXIDANT; REAGENT; SURFACE; ESTERS; MILD;
D O I
10.1039/c3ra41996g
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An efficient aerobic chemoselective oxidation of thiols to disulfides has been achieved under ball-milling over neutral aluminium oxide (grinding auxiliary) in the absence of any catalyst, co-oxidant, solvent, or base. A wide variety of functionalized diaryl, diheteroaryl and dialkyl disulfides have been obtained in high yields.
引用
收藏
页码:10680 / 10686
页数:7
相关论文
共 62 条
[1]   Diethylamine-Catalyzed Dimerization of Thiols: An Inexpensive and Green Method for the Synthesis of Homodisulfides Under Aqueous Conditions [J].
Abaee, M. Saeed ;
Mojtahedi, Mohammad M. ;
Navidipoor, Somayeh .
SYNTHETIC COMMUNICATIONS, 2011, 41 (02) :170-176
[2]   Green methodology for the preparation of disulfide [J].
Attri, Pankaj ;
Gupta, Shweta ;
Kumar, Rupesh .
GREEN CHEMISTRY LETTERS AND REVIEWS, 2012, 5 (01) :33-42
[3]   Development of a tandem base-catalyzed, triphenylphosphine-mediated disulfide reduction-Michael addition [J].
Bartolozzi, Alessandra ;
Foudoulakis, Hope M. ;
Cole, Bridget M. .
SYNTHESIS-STUTTGART, 2008, (13) :2023-2032
[4]   Synthesis, catalytic and antibacterial activity of 2-aminophenyldisulphide [J].
Bhowon, M. Gupta ;
Jhaumeer-Laulloo, S. ;
Soukhee, N. ;
Allibacus, A. ;
Shiboo, V. .
JOURNAL OF COORDINATION CHEMISTRY, 2007, 60 (12) :1335-1343
[5]   2,4-Dinitrophenyl 4-methoxybenzyl disulfide: A new efficient reagent for the electrophilic sulfenylation of beta-amino ester enolates [J].
Bischoff, L ;
David, C ;
Martin, L ;
Meudal, H ;
Roques, BP ;
FournieZaluski, MC .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (14) :4848-4850
[6]   Environmentally benign peptide synthesis using liquid-assisted ball-milling: application to the synthesis of Leu-enkephalin [J].
Bonnamour, Julien ;
Metro, Thomas-Xavier ;
Martinez, Jean ;
Lamaty, Frederic .
GREEN CHEMISTRY, 2013, 15 (05) :1116-1120
[7]   A highly advantageous metal-free approach to diaryl disulfides in water [J].
Carril, Monica ;
SanMartin, Raul ;
Dominguez, Esther ;
Tellitu, Imanol .
GREEN CHEMISTRY, 2007, 9 (04) :315-317
[8]   An efficient and convenient method for preparation of disulfides from thiols using air as oxidant catalyzed by Co-Salophen [J].
Chai, Pin Ji ;
Li, Yong Shu ;
Tan, Cheng Xia .
CHINESE CHEMICAL LETTERS, 2011, 22 (12) :1403-1406
[9]   Solvent-free transesterification in a ball-mill over alumina surface [J].
Chatterjee, Tanmay ;
Saha, Debasree ;
Ranu, Brindaban C. .
TETRAHEDRON LETTERS, 2012, 53 (32) :4142-4144
[10]   N-phenyltriazolinedione as an efficient, selective, and reusable reagent for the oxidation of thiols to disulfides [J].
Christoforou, Angelos ;
Nicolaou, Georgia ;
Elemes, Yiannis .
TETRAHEDRON LETTERS, 2006, 47 (52) :9211-9213