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Published on: January 3, 2018
Photodecarboxylative C-H Alkylation of Azauracils with N-(Acyloxy)phthalimides
Satya Prakash Panda1, Sudhir Kumar Hota1, Rupashri Dash1
1Department of Chemistry, Indian Institute of Technology Jodhpur, Karwar, Rajasthan 342037, India.
Abstract:
We disclose a transition-metal-free NaI/PPh3-mediated direct C-H alkylation of azauracils using N-(acyloxy)pthalimides (NHPIs) as readily available alkyl surrogates under visible light irradiation. Detailed mechanistic studies reveal formation of a photoactivated electron donor-acceptor (EDA) complex between NaI/PPh3, TMEDA, and alkyl NHPI ester and establish the crucial role of TMEDA in increasing the activity of the photoredox system. The reaction demonstrates a broad scope, scalability, and appreciable functional group tolerance. A variety of azauracils are shown to undergo alkylation by primary, secondary, and tertiary NHPI esters under mild conditions, furnishing the desired products in good to excellent yields.
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