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Synthesis of Disulfides
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The reaction of a thiol with 1-chlorobenzotriazole (BtCl) affords the
benzotriazolated thiol (RSBt) without appreciable formation of the
symmetrical disulfide. RSBt reacts with another thiol to form the
unsymmetrical disulfide in a one-pot sequence without the need for toxic and
harsh oxidizing agents.
R. Hunter, M. Caira, N. Stellenboom, J. Org. Chem., 2006, 71, 8268-8271.
The reaction of a thiol with 1-chlorobenzotriazole (BtCl) affords the
benzotriazolated thiol (RSBt) without appreciable formation of the
symmetrical disulfide. RSBt reacts with another thiol to form the
unsymmetrical disulfide in a one-pot sequence without the need for toxic and
harsh oxidizing agents.
R. Hunter, M. Caira, N. Stellenboom, J. Org. Chem., 2006, 71, 8268-8271.
N-Thiohydroxy succinimide esters (NTSEs) are versatile reagents,
serving as both acyl and acylthio surrogates for the diverse synthesis of
ketones, thioesters, amides, and acyl disulfides by selective cleavage of
similarly reactive C-S and N-S bonds.
Y.-F. Li, Y.-F. Wei, J. Tian, J. Zhang, H.-H. Chang, W.-C. Gao, Org. Lett.,
2022, 24, 5736-5740.
Unsymmetrical disulfides have been prepared from the corresponding thiols and
bis-(5,5-dimethyl-2-thiono-1,3,2-dioxaphosphorinanyl)disulfide under mild
conditions with very good yields. This method can be applied to thiols bearing
neutral, aromatic, basic or acidic functionalities with variable length of
carbon chain.
S. Antoniow, D. Witt, Synthesis, 2007, 363-366.
A convenient method for the synthesis of unsymmetrical disulfides under mild
conditions in good to excellent yields is based on the use of a readily
available organophosphorus sulfenyl bromide as activating agent. The
unsymmetrical disulfides can be obtained for l-cysteine derivatives and thiols
bearing neutral, basic, or acidic functionalities.
M. Szymelfejnik, S. Demkowicz, J. Rachon, D. Witt, Synthesis, 2007,
3528-3534.
The combination of a riboflavin-derived organocatalyst and molecular iodine
successfully promoted the aerobic oxidation of thiols to disulfides under
metal-free mild conditions at room temperature. The the biomimetic flavin
catalyst enables the transfer of electrons from the iodine forming the basis for
a green oxidative synthesis of disulfides from thiols.
M. Oka, R. Kozako, H. Iida, Synlett, 2021,
32,
1227-1230.
The reaction of aryl halides with ethyl potassium xanthogenate in the presence
of MOF-199 provides O-Ethyl-S-aryl carbonodithioates as
intermediates, that can be converted into symmetrical diaryl disulfides,
unsymmetrical aryl alkyl(aryl′) disulfides by the reaction with S-alkyl(aryl)
sulfurothioates (Bunte salts) as well as unsymmetrical aryl alkyl(aryl′)
sulfides.
M. Soleiman-Beigi, Z. Arzehgar,
Synlett, 2018, 29, 986-992.
N-Trifluoroacetyl arenesulfenamides are effective precursors for the
synthesis of unsymmetrical disulfides and sulfenamides. Reactions of N-trifluoroacetyl arenesulfenamides
with thiols and amines gave the desired products in high yields within short
reaction times.
M. Bao, M. Shimizu, Tetrahedron, 2003, 59, 9655-9659.
The use of sodium in silica gel enables an efficient synthesis of symmetrical
disulfanes from organic thiocyanates at room temperature. This protocol provides
an attractive alternative to existing methods for the preparation of symmetrical
disulfanes as it avoids the use of foul-smelling thiols.
C. K. Maurya, A. Mazumder, A. Kumar, P. K. Gupta,
Synlett, 2016, 27, 409-411.
An organodiselenide catalyzed the aerobic oxidation of thiols into disulfides
in practical yields without any reagents/additives, base, and light source. The
synthesized diselenide also catalyzes the reduction of hydrogen peroxide into
water.
V. Rathore, A. Upadhyay, S. Kumar, Org. Lett.,
2018, 20, 6274-6278.
Thiols were effectively oxidized into disulfides by reacting with hydrogen
peroxide in the presence of a catalytic amount of iodide ion or iodine.
M. Kirihara, Y. Asai, S. Ogawa, T. Noguchi, A. Hatano, Y. Hirai, Synthesis, 2007,
3286-3289.
Selective and quantitative conversion of thiols to disulfides was effected
by dimethyl sulfoxide under mild conditions catalyzed by
dichlorodioxomolybdenum(VI).
R. Sanz, R. Aguado, M. R. Pedrosa, F. Arnáiz, Synthesis, 2002, 856-858.
A mild and efficient oxidation of various thiols affords the corresponding
disulfides using 1,3-dibromo-5,5-dimethylhydantoin (DBDMH) as oxidant under both
solution and solvent-free conditions.
A. Khazaei, M. A. Zolfigol, A. Rostami, Synthesis,
2004, 2959-2961.