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Synthesis 2007(22): 3507-3511  
DOI: 10.1055/s-2007-990827
PAPER
© Georg Thieme Verlag Stuttgart · New York

Ceric Ammonium Nitrate Catalyzed Oxidation of Sulfides to Sulfoxides

Mohammed Hashmat Ali*, Donna Kriedelbaugh, Timothy Wencewicz
Chemistry Department, Southeast Missouri State University, One University Plaza, Cape Girardeau, MO 63701, USA
Fax: +1(573)9866433; e-Mail: mhali@semo.edu;
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Publication History

Received 1 March 2007
Publication Date:
16 October 2007 (online)

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Abstract

Oxidation of sulfides to sulfoxides with a catalytic amount of ceric ammonium nitrate (CAN) reagent supported on silica gel has been achieved. Stoichiometric sodium bromate is utilized as the primary oxidant to continue the catalytic cycle involving CAN. Solid-supported CAN reagent allowed us to avoid using aqueous reaction media generally employed in CAN-promoted reactions. This heterogeneous CAN/NaBrO3 reagent has simplified the reaction work-up and product isolation, produced higher product yields, and shortened reaction times compared to reactions with homogeneous CAN reagents employing aqueous media.

Key words

silica gel - solid support - CAN - sulfide - sulfoxide