Csp–Csp bond cleavage and fragment coupling: a transition metal-free “extrusion and recombination” approach towards synthesis of 1,2-diketones

Abstract

A metal-free C–C bond activation strategy of 1,3-diynes has been described via an “extrusion and recombination” approach, which delivered structurally important 1,2-diketones. This phenomenon was performed using tetra-n-butylammonium iodide (TBAI) as a catalyst and peroxide as a radical initiator and oxidant. The C–C bond activation follows sequential oxidation, extrusion of CO2 as a byproduct and sewing of the molecular fragments to release the desired products. This protocol was elaborated towards unsymmetrical 1,2-diketones via selective generation and recombination of distinct molecular fragments. The proposed mechanism has been verified using adequate control experiments and DFT calculations.

Graphical abstract: Csp–Csp bond cleavage and fragment coupling: a transition metal-free “extrusion and recombination” approach towards synthesis of 1,2-diketones

Supplementary files

Article information

Article type
Research Article
Submitted
08 Jun 2021
Accepted
30 Jul 2021
First published
30 Jul 2021

Org. Chem. Front., 2021, Advance Article

Csp–Csp bond cleavage and fragment coupling: a transition metal-free “extrusion and recombination” approach towards synthesis of 1,2-diketones

R. Gujjarappa, N. Vodnala, A. Kandpal, L. Roy, S. Gupta and C. C. Malakar, Org. Chem. Front., 2021, Advance Article , DOI: 10.1039/D1QO00848J

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