Anti-Markovnikov Hydroazidation of Activated Olefins via Organic Photoredox Catalysis
Nicholas P. R. Onuska, Megan E. Schutzbach-Horton, José L. Rosario Collazo, David. A. Nicewicz*
*Department of Chemistry, The University of North Carolina at
Chapel Hill, NC, 27599-2390, USA,
Email: nicewicz
unc.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
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
