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UV Light-Mediated Generation of Ketyl Radicals with a Concurrent 1,2-Boron Shift and One-Pot Synthesis of
Kankanala Naveen Kumar1, Chandrakant Sahu1, Pranjal Mahindrakar2
1Department of Medicinal Chemistry, Centre for Marine Therapeutics (CMT), and Centre of Excellence in Flow Chemistry and Continuous Manufacturing, National Institute of Pharmaceutical Education and Research-Kolkata, 168, Maniktala Main Road, Kolkata 700054, India.
Abstract:
The photocatalyzed reactions using metal and organic photocatalysts generate ketyl radicals by a single-electron transfer, proton-coupled electron transfer mechanism. Photocatalyst-free UV light-mediated generation of ketyl radicals in the presence of bis(pinacoloto)diboron (B2pin2) is developed. The addition of the Bpin radical to a carbonyl group followed by a 1,2-boron shift generated a thermodynamically favorable ketyl radical. This method was applied to the one-pot synthesis of benzoxaboroles from o-halo benzaldehydes.
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