Transition metal-catalyzed cross-coupling of sp2 C-H bonds with diazo compounds via carbene migratory insertion represents an efficient strategy for the construction of C-C and C-heteroatom bonds in organic synthesis. Despite the popularity of diazo compounds as coupling partners in C-H activation, they pose serious safety and stability issues due to potential exothermic reactions linked with the release of N2 gas. However, compared with diazo compounds, sulfoxonium ylides are generally crystalline solids, more stable, widely used in industrial scales, and easier/safer to prepare. Therefore, recent years have witnessed an upsurge in employing α-carbonyl sulfoxonium ylides as an alternative carbene surrogate in transition metal-catalyzed C-H activation. Unlike diazo compounds, α-carbonyl sulfoxonium ylides contain inherent potential to serve as a coupling partner as well as a weak directing group. This review will summarize the progress made in both categories of reactions.

α-Carbonyl sulfoxonium ylides in transition metal-catalyzed C-H activation: a safe carbene precursor and a weak directing group.

Research Progress of Sulfoxonium Ylides in the Construction of Five/Six-Membered Nitrogen-Containing Heterocycles

Pyridine is a crucial heterocyclic scaffold that is widely found in organic chemistry, medicines, natural products, and functional materials. In spite of the discovery of several methods for the synthesis of functionalized pyridines or their integration into an organic molecule, new methodologies for the direct functionalization of pyridine scaffolds have been developed during the past two decades. In addition, transition-metal-catalyzed C–H functionalization and rare earth metal-catalyzed reactions have flourished over the past two decades in the development of functionalized organic molecules of concern. In this review, we discuss recent achievements in the transition-metal and rare earth metal-catalyzed C–H bond functionalization of pyridine and look into the mechanisms involved.

Pyridine C(sp2)–H bond functionalization under transition-metal and rare earth metal catalysis

In this work, a Rh(I)-catalyzed C3-alkenylation of 2,2'-bipyridine-6-carboxamide with terminal and internal alkynes was developed, providing an efficient access to a broad range of alkenylated 2,2'-bipyridine derivatives with exclusive regioselectivity and stereoselectivity. Deuterium labeling experiments indicate that an irreversible rollover C−H activation process was involved in this reaction.

Rhodium(I)-Catalyzed Regioselective C−H Alkenylation of 2,2′-Bipyridine Derivatives with Alkynes

Three short and efficient total syntheses of cassiarin C are reported, from a chromanone common key intermediate. A C-H activation strategy, under rhodium catalysis on its pivaloyl oxime, enabled the installation of the pyridine ring. Dehydrogenation of 8- 

A rhodium-catalyzed C‒H activation/cyclization approach toward the total syntheses of cassiarin C and 8-O-methylcassiarin A from a common intermediate

A novel protocol for Rh(iii)-catalyzed switchable C-H acylmethylation and annulation of 2,2'-bipyridine derivatives with sulfoxonium ylides is reported. This protocol provides a facile approach to synthesize structurally diverse acylmethylated 2,2'-bipyridine derivatives and acyl pyrido[2,3-a]indolizines with a broad range of functional group tolerance.

Rhodium(iii)-catalyzed switchable C-H acylmethylation and annulation of 2,2'-bipyridine derivatives with sulfoxonium ylides.

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Rhodium(iii)-catalyzed switchable C-H acylmethylation and annulation of 2,2'-bipyridine derivatives with sulfoxonium ylides.