Catalytic Functionalization of Metallocarbenes Derived from α‐Diazocarbonyl Compounds and Their Precursors. Issue 12 (26th August 2021)

• Record Type: Journal Article
• Authors: Yadagiri, Dongari; Anbarasan, Pazhamalai
• Is Part Of: Chemical record. Volume 21:Issue 12(2021)
• Page Start: 3872
• Page End: 3883
• Publication Date: 2021-08-26
• Subjects: azavinyl carbenes -- triazoles -- diazocarbonyl compounds -- rhodium -- heterocyclic compounds; Chemistry -- Periodicals; 540
• DOI: 10.1002/tcr.202100167
• Languages: English
• ISSNs: 1527-8999

Abstract

Abstract: 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 α‐diazocarbonyl compounds, which are the precursors for α‐imino (carbonyl) metal carbenes in the presence of transition metal catalysts. Functionalization of α‐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. Abstract : In this personal account, we described our contribution in the selective functionalization of N ‐sulfonyl‐1, 2, 3‐triazoles and α ‐diazo carbonyl compounds. In the presence of suitable transition metal catalyst and nucleophiles, versatile ylides are generated via α ‐imino(carbonyl) metal carbenes. Functionalization of ylides through either trapping with non‐polar bonds, rearrangement or cycloaddition, and 1, 3‐insertion led to the efficient synthesis of heterocyclic compounds and beyond.