Superelectrophilic Activation of Phenylglyoxamides: Efficient Synthesis of Triarylacetamides and Fluorenecarboxamides by Superacid Catalysis

Direct synthesis of triarylacetamides and 9-fluorenecarboxamides has been achieved. Phenylglyoxamides upon superelectrophilic activation in trifluoromethanesulfonic acid (triflic acid, TFSA) leads to Friedel–Crafts hydroxyalkylation or one-pot tandem hydroxyalkylation-4 π -electrocyclization of arom...

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Bibliographic Details
Published in:Topics in catalysis 2018-06, Vol.61 (7-8), p.652-663
Main Authors: Narayanan, Arjun, Nirmalchandar, Archith, Paknia, Farzaneh, Rasul, Golam, Mathew, Thomas, Surya Prakash, G. K.
Format: Article
Language:English
Subjects:
Activation
Catalysis
Characterization and Evaluation of Materials
Chemical synthesis
Chemistry
Chemistry and Materials Science
Industrial Chemistry/Chemical Engineering
Original Paper
Pharmacy
Physical Chemistry
Triflic acid
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Summary:Direct synthesis of triarylacetamides and 9-fluorenecarboxamides has been achieved. Phenylglyoxamides upon superelectrophilic activation in trifluoromethanesulfonic acid (triflic acid, TFSA) leads to Friedel–Crafts hydroxyalkylation or one-pot tandem hydroxyalkylation-4 π -electrocyclization of aromatics into triarylacetamides or 9-fluorenecarboxamides, respectively. Mechanistic investigation by DFT calculations suggests the intermediacy of diprotonated (or “protosolvated”) intermediates.
ISSN:1022-5528
1572-9028
DOI:10.1007/s11244-018-0962-x