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Issue 7, 2017
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Chemoselective acyl C–O bond activation in esters for Suzuki–Miyaura coupling

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Abstract

Exploitation of the low binding affinity of NHC–palladium complex for the carbonyl oxygen of ester to form three-centered transition state led to the discovery of Suzuki–Miyaura coupling via unprecedented C(acyl)–O bond cleavage. The use of bulky NHC ligand resulted in direct coupling as it prevented decarbonylation of ester. This access to alternative chemoselectivity by careful selection has extended the synthetic portfolio of esters for the diversification of interesting molecular scaffolds.

Graphical abstract: Chemoselective acyl C–O bond activation in esters for Suzuki–Miyaura coupling

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Publication details

The article was received on 24 Jan 2017, accepted on 16 Mar 2017 and first published on 20 Mar 2017


Article type: Highlight
DOI: 10.1039/C7QO00068E
Citation: Org. Chem. Front., 2017,4, 1430-1434
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    Chemoselective acyl C–O bond activation in esters for Suzuki–Miyaura coupling

    M. Mondal, T. Begum and U. Bora, Org. Chem. Front., 2017, 4, 1430
    DOI: 10.1039/C7QO00068E

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