4.6 Article

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

期刊

CHEMICAL RECORD
卷 21, 期 12, 页码 3872-3883

出版社

WILEY-V C H VERLAG GMBH
DOI: 10.1002/tcr.202100167

关键词

azavinyl carbenes; triazoles; diazocarbonyl compounds; rhodium; heterocyclic compounds

资金

  1. DST-Science and Engineering Research Board (DST-SERB), New Delhi [SR/S1/OC-48/2012, EMR/2016/003677, CRG/2020/004644]

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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.
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.

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