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Anti-Markovnikov Hydroazidation of Activated Olefins via Organic Photoredox Catalysis

Nicholas P. R. Onuska, Megan E. Schutzbach-Horton, Josť L. Rosario Collazo, David. A. Nicewicz*

*Department of Chemistry, The University of North Carolina at Chapel Hill, NC, 27599-2390, USA, Email: nicewiczunc.edu

N. P. R. Onuska, M. E. Schutzbach-Horton, J. L. R. Collazo, D. A. Nicewicz, Synlett, 2020, 31, 55-59.

DOI: 10.1055/s-0039-1690691 (free Supporting Information)


Abstract

An organic acridinium salt catalyzes an anti-Markovnikov hydroazidation of activated olefins  under irradiation from blue LEDs. This method is applicable to a variety of substituted styrenes and several vinyl ethers, yielding synthetically versatile hydroazidation products in excellent yield, whereas terminal styrenes provide hydroazidation products in moderate yields.

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Key Words

photooxidation, alkenes, azides, radicals, regioselectivity, photochemistry, organocatalysis


ID: J72-Y2020