Indium(0)-Mediated C sp 3-S/O Cross-Coupling Approach Towards the Regioselective Alkylation of α-Enolic Esters/Dithioesters: A Mechanistic Insight

Chowdhury, Sushobhan ; Chanda, Tanmoy ; Gupta, Ashutosh ; Koley, Suvajit ; Ramulu, B. Janaki ; Jones, Raymond C. F. ; Singh, Maya Shankar (2014) Indium(0)-Mediated C sp 3-S/O Cross-Coupling Approach Towards the Regioselective Alkylation of α-Enolic Esters/Dithioesters: A Mechanistic Insight European Journal of Organic Chemistry, 2014 (14). pp. 2964-2971. ISSN 1434-193X

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Official URL: http://doi.org/10.1002/ejoc.201301788

Related URL: http://dx.doi.org/10.1002/ejoc.201301788

Abstract

An indium(0)-mediated Curn:x-wiley:1434193X:media:EJOC201301788:tex2gif-inf-4–S/O cross-coupling reaction that proceeds without added co-catalyst or promoter leads to the highly regioselective alkylation of α-enolic acetate/dithioacetate systems. The selectivity for C-, S-, or O-alkylation is dependent on the nucleophilic behavior of α-enolic acetate/dithioacetate system and was further supported by DFT calculations.

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