ECS Meeting Abstracts, 19(MA2014-01), p. 829-829, 2014
Wiley, Chemistry - A European Journal, 40(20), p. 12740-12744, 2014
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An electrochemical approach to the intramolecular aminooxygenation of unactivated alkenes has been developed. This process is based on the addition of nitrogen-centered radicals, generated through electrochemical oxidation, to alkenes followed by trapping of the cyclized radical intermediate with 2,2,6,6-tetramethylpiperidine-N-oxyl radical (TEMPO). Difunctionalization of a variety of alkenes with easily available carbamates/amides and TEMPO affords aminooxygenation products in high yields and with excellent trans selectivity for cyclic systems (d.r. up to>20:1). The approach provides a much-needed complementary route to existing cis-selective methods. ? 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.