KSO promoted metal-free direct C-alkylation of acetophenones with alcohols

Herein, we report a metal-free synthetic methodology for the C-alkylation of acetophenones following a hydrogen borrowing-like pathway using the commercially available inorganic oxidant K 2 S 2 O 8 in conjunction with KO t Bu. This study articulates the potential of K 2 S 2 O 8 in fast initiation of...

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Published in:Organic & biomolecular chemistry 2023-12, Vol.21 (48), p.9519-9523
Main Authors: Gautam, Deepak, Gahlaut, Puneet Singh, Pathak, Shristi, Jana, Barun
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Summary:Herein, we report a metal-free synthetic methodology for the C-alkylation of acetophenones following a hydrogen borrowing-like pathway using the commercially available inorganic oxidant K 2 S 2 O 8 in conjunction with KO t Bu. This study articulates the potential of K 2 S 2 O 8 in fast initiation of the oxidation of benzyl alcohols to develop an atom-economical, easy, and more efficient methodology for the C-alkylation of various acetophenones and synthesis of a variety of substituted quinolines. Experimental data from control experiments, literature and characterization of intermediates through spectroscopic techniques support the proposed plausible mechanism. A metal-free synthetic methodology for the C-alkylation of acetophenones following a hydrogen borrowing-like pathway using the commercially available inorganic oxidant K 2 S 2 O 8 in conjunction with KO t Bu is reported.
ISSN:1477-0520
1477-0539
DOI:10.1039/d3ob01526b