Recent Applications of α-Carbonyl Sulfoxonium Ylides in Rhodium- and Iridium-Catalyzed C–H Functionalizations

Abstract

Sulfoxonium ylides are a special type of sulfur ylides that serve as new C1 or C2 synthons recently developed for use in C–H functionalization to access acylmethylated or cyclized compounds through the formation of metal carbene species. Many excellent works have reported the syntheses of various useful skeletons from these versatile synthons. These developments have not previously been completely investigated or reviewed. In this review, we summarize recent advances in the use of α-carbonyl sulfoxonium ylides in C–H functionalizations, including ortho-C–H acylmethylation reactions and ortho-C–H activation/cyclization reactions.

Table of Contents

1 Introduction

2 Ortho-C–H Acylmethylation Reactions

3 Ortho-C–H Activation/Cyclization Reactions

3.1 Ortho-C–H Activation/Cyclization of Anilines and Enamines

3.2 Ortho-C–H Activation/Cyclization of Azobenzenes

3.3 Ortho-C–H Activation/Cyclization of N-Methoxybenzamide

3.4 Ortho-C–H Activation/Cyclization of Imines

3.5 Ortho-C–H Activation/Cyclization of N-Azoloimines

3.6 Ortho-C–H Activation/Cyclization of Benzoylacetonitriles

3.7 Ortho-C–H Activation/Cyclization of Benzoyl Sulfoxonium Ylides

4 Conclusion

Key words

sulfur ylides - C–H functionalization - acylmethylation - ­cyclization - metal carbenes

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