K2S2O8 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 K2S2O8 in conjunction with (KOBu)-Bu-t. This study articulates the potential of K2S2O8 in fast initiation of the o...

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Published inOrganic & biomolecular chemistry Vol. 21; no. 48; pp. 9519 - 9523
Main Authors Gautam, Deepak, Gahlaut, Puneet Singh, Pathak, Shristi, Jana, Barun
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 13.12.2023
Royal Society of Chemistry
Subjects
Alkylation
Benzyl alcohol
Chemistry
Chemistry, Organic
Intermediates
Organic compounds
Oxidants
Oxidation
Oxidizing agents
Physical Sciences
Potassium persulfate
Quinolines
Science & Technology
KETONES
HYDROGEN
N-ALKYLATION
CATALYZED ALPHA-ALKYLATION
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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 K2S2O8 in conjunction with (KOBu)-Bu-t. This study articulates the potential of K2S2O8 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.
Bibliography:ObjectType-Article-1
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ISSN:1477-0520
1477-0539
DOI:10.1039/d3ob01526b