ACS Catalysis
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Notes
chemoselective reducing agent for sulfoxides. Green Chem.
2013, 15, 999–1005.
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The authors declare no competing financial interest
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(a) Chasar, D. W. Quantitative reduction of sulfoxides. J.
Org. Chem. 1971, 36, 613–614. (b) Drabowiz, J.; Mikola-
jczyk, M. A mild and efficient reduction of sulphoxides by
means of lithium alanate and titanium(IV) chloride. Synthesis
1976, 527–528. (c) Harrison, D. J.; Tam, N. C.; Vogels, C.
M.; Langler, R. F.; Baker, R. T.; Decken, A.; Westcott, S. A.
A gentle and efficient route for the deoxygenation of sulfox-
ides using catecholborane (HBcat; cat = 1,2-O C H ). Tetra-
2 6 4
hedron Lett. 2004, 45, 8493–8496. (d) Zhang, J.; Gao, X.;
Zhang, C.; Zhang, C.; Luan, J.; Zhao, D. Mild and efficient
deoxygenation of sulfoxides to sulfides using HfCl /KBH
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Supporting Information
The Supporting Information is available free of charge on the ACS
Publications website.
Experimental procedures and characterization data for all new
compounds (PDF)
ACKNOWLEDGMENT
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The authors would like to thank the EPSRC (A.K.C.
EP/R013748/1), the University of York (J.A.R.-A., W.P.U.) and
the Leverhulme Trust (for an Early Career Fellowship, ECF-2015-
system. Synth. Commun. 2010, 40, 1794–1801.
6. (a) Aida, T.; Furukawa, N.; Oae, S. Catalytic reduction of di-
methyl sulfoxide and other sulfoxides with bromine - hydro-
bromic acid system. Tetrahedron Lett. 1973, 14, 3853–3856.
(b) Landini, D.; Maia, A. M.; Rolla, F. Racemization of
sulphoxides with halide ions anchimerically assisted by a car-
boxy-group. The different behaviour of chloride and bromide
ions. J. Chem. Soc., Perkin Trans. 2 1976, 1288–1291. (c)
Firouzabadi, H.; Karimi, B. Efficient deoxygenation of sul-
foxides to thioethers and reductive coupling of sulfonyl chlo-
rides to disulfides with tungsten hexachloride. Synthesis 1999,
500–502. (d) Shimizu, M.; Shibuya, K.; Hayakawa, R.
Chemoselective deoxygenation of sulfoxides with titanium
tetraiodide. Synlett 2000, 1437–1438. (e) Yoo, B. W.; Choi,
K. H.; Kim, D. Y.; Choi, K. I.; Kim, J. H. Mild and efficient
reduction of sulfoxides to sulfides with titanium tetrachlo-
ride–indium system. Synth. Commun. 2003, 33, 53–57. (f)
Iranpoor, N.; Firouzbadi, H.; Shaterian, H. R. A new ap-
proach to the reduction of sulfoxides to sulfides with 1,3-di-
thiane in the presence of electrophilic bromine as catalyst. J.
Org. Chem. 2002, 67, 2826–2830.
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13, W.P.U.) for financial support. We are also grateful for the pro-
vision of an Eleanor Dodson Fellowship (to W.P.U.) by the Depart-
ment of Chemistry, University of York. We also thank Dr. James
R. Donald, Dr. Michael J. James, Prof. Robin Perutz, Dr. Richard
E. Douthwaite and Prof. Anne-Kathrin Duhme-Klair for insightful
discussions and Mr. Alex Derry for help with preliminary work.
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