Organosulfur compounds have long
played a vital role in organic
chemistry and in the development of novel chemical structures and
architectures. Prominent among these organosulfur compounds are those
involving a sulfur(IV) center, which have been the subject of countless
investigations over more than a hundred years. In addition to a long
list of textbook sulfur-based reactions, there has been a sustained
interest in the chemistry of organosulfur(IV) compounds in recent
years. Of particular interest within organosulfur chemistry is the
ease with which the synthetic chemist can effect a wide range of transformations
through either bond formation or bond cleavage at sulfur. This review
aims to cover the developments of the past decade in the chemistry
of organic sulfur(IV) molecules and provide insight into both the
wide range of reactions which critically rely on this versatile element
and the diverse scaffolds that can thereby be synthesized.
A ruthenium‐catalysed cross‐olefination of diazo compounds and sulfoxonium ylides is presented. Our reaction design exploits the intrinsic difference in reactivity of diazo compounds and sulfoxonium ylides as both carbene precursors and nucleophiles, which results in a highly selective reaction.
Traditionally employed in the synthesis of small ring systems and rearrangement chemistry, sulfur-based ylides occupy a unique position in the toolbox of the synthetic organic chemist. In recent years a number of pioneering researchers have looked to expand the application of these unorthodox reagents through the use of transition metal catalysis. The strength and flexibility of such a combination have been shown to be of key importance in developing powerful novel methodologies. This chapter summarises recent developments in transition metal-catalysed sulfonium/sulfoxonium ylide reactions, as well as providing a historical perspective. In overviewing the successes in this area, the authors hope to encourage others into this growing field.
The Rh-catalyzed hydroacylative union of aldehydes and o-alkynyl anilines leads to 2-aminophenyl enones, and onward to substituted quinolines. The mild reaction conditions employed in this chemistry result in a process that displays broad functional group tolerance, allowing the preparation of diversely substituted quinolines in high yields. Extension to the use of o-alkynyl nitro arenes as substrates leads to 2-nitrochalcones, from which both quinolines and quinoline N-oxides can be accessed.
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