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Chemoselective Synthesis of Aryl Ketones from Amides and Grignard Reagents via C(O)-N Bond Cleavage under Catalyst-Free Conditions

Popuri Sureshbabu, Sadaf Azeez, Nalluchamy Muniyappan, Shahulhameed Sabiah and Jeyakumar Kandasamy*

*Department of Chemistry, Indian Institute of Technology (BHU), Varanasi, Uttar Pradesh 221005, India, Email:

P. Sureshbabu, S. Azeez, N. Muniyappan, S. Sabiah, J. Kandasamy, J. Org. Chem., 2019, 84, 11823-11838.

DOI: 10.1021/acs.joc.9b01699

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The reaction of different aryl, alkyl, and alkynyl Grignard reagents with N-Boc amides provides a wide range of aryl ketones via chemoselective C(O)-N bond cleavage under catalyst-free conditions. α-Ketoamide was successfully converted to aryl diketones, while α,β-unsaturated amide underwent 1,4-addition followed by C(O)-N bond cleavage to provide diaryl propiophenones.

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Key Words

aryl ketones, Grignard reagents

ID: J42-Y2019