4
proposed reaction mechanism. On the same analogy, it is
Supplementary data
proposed that alkyl hypobromothioite (2c) is the plausible
reactive intermediate in case of disulfane synthesis.
Electronic supplementary (ESI) available as a separate file.
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Scheme-5: Controlled experiments with isolated sulfonyl
bromide
Conclusion
In summary, we have achieved a generalized economic approach
towards synthesis of thiosulfonates, sulfonamides and disulfanes
-the “Trio”in an open air, sustainable metal free reaction
conditions. Phenyl trimethyl ammonium tribromide (PTAB) has
been identified as an effective reagent for these oxidative
couplings. Gram scale transformation to chiral sulfonamides and
sulfanes were carried out successfully making it industrially
important. The sulfonamides and disulfanes can be achieved in
gram scale making it industrially important. The disulfanes were
achieved without column chromatography just after the reaction
with adequate purity. Thus the synthetic methodology prescribed
in this manuscript fulfills all our expectations to realize a facile
open air sustainable reaction methodology. The protocol further
resemble a metal-free reaction in shorter timescale. All these
advantages brands this methodology as the best of the available
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Acknowledgements
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Fu, L.; Bao, X.; Li, S.; Wang, L.; Liu, Z.; Chen, W.; Xia, Q.;
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We sincerely acknowledge Department of Science and
Technology (DST), Govt. of India (Grant nos SB/FT/CS-
076/2012)& EEQ/2016/000518, Board of Research in Nuclear
Sciences (BRNS) (2013/20/37C/2/BRNS/2651), and INSPIRE-
DST, Govt. of India (Grant No.04/2013/000751).MKG thanks
NIT Rourkela for research fellowship. NR thanks DST for
fellowship.
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