Catalytic Functionalization of Metallocarbenes Derived from α-Diazocarbonyl Compounds and Their Precursors

Short and efficient synthesis of heterocyclic compounds are highly desirable in synthetic organic chemistry. It is a dream approach to accomplish these syntheses from readily available starting materials in a single step. In this personal account, we discuss our contribution in the synthesis of heterocyclic compounds and beyond from N-sulfonyl-1,2,3-triazoles and alpha-diazocarbonyl compounds, which are the precursors for alpha-imino (carbonyl) metal carbenes in the presence of transition metal catalysts. Functionalization of alpha-imino(carbonyl) metal carbenes has been achieved through in-situ generated metal-stabilized ylides followed by either intramolecular trapping by non-polar bonds, rearrangement, cycloaddition, or 1,3-insertion fashion, which led to the efficient synthesis of various synthetically important intermediates and heterocyclic compounds.

Automated summary

This article discusses the synthesis of heterocyclic compounds starting from N-sulfonyl-1,2,3-triazoles and alpha-diazocarbonyl compounds using transition metal catalysts. Functionalization of alpha-imino(carbonyl) metal carbenes has been achieved through in-situ generated metal-stabilized ylides, leading to the efficient synthesis of various synthetically important intermediates and heterocyclic compounds.