Electricity mediated [3+2]-cycloaddition of N-sulfonylcyclopropanes with olefins via N-centered radical intermediates: access to cyclopentane analogs DEBARSHI Saha, Irshad Maajid Taily, Nakshatra Banerjee, Prabal Banerjee Indian Institute of Technology, India Anovel route for the exploitation of cyclopropanes has been devised and involves electrochemical Csp3 –Csp3 bond cleavage, enabling the [3+2] cycloaddition with olefins to render the di- and tri-substituted cyclopentane adducts. Additionally, the reaction features the synthesis of azaarene substituted derivatives and provides access to an all-carbon quaternary center. Moreover, the protocol circumvents the employment of harmful exogenous oxidants and utilizes the potential of traceless electrons. Further, mechanistic studies corroborate the significance of the N-center radical and also suggest that the sulfonyl group plays a paramount role in the designed methodology. Eventually, the cyclopentane products were subjected to synthetically useful downstream modifications revealing the utility of the obtained product. References 1. D. Saha, I.M. Taily, N. Banerjee and P. Banerjee;Electricity mediatd [3+2]-cycloaddition of N-sulfonylcyclopropanes with olefins via N-centered radical intermediates: access to cyclopentane analogs, Chem. Commun. , 2022, 58 , 5459-5462.
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