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Oxidation of Nonactivated Anilines to Generate N-Aryl Nitrenoids

Tianning Deng, Wrickban Mazumdar, Russell L. Ford, Navendu Jana, Ragda Izar, Donald J. Wink and Tom G. Driver*

*Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, Illinois 60607-7061, United States, Email:

T. Deng, W. Mazumdar, R. L. Ford, N. Jana, R. Izar, D. J. Wink, T. G. Driver, J. Am. Chem. Soc., 2020, 142, 4456-4463.

DOI: 10.1021/jacs.9b13599

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A low-temperature, protecting-group-free oxidation of 2-substituted anilines with PIFA in the presence of an acid generates an electrophilic N-aryl nitrenoid intermediate that can engage in C-NAr bond formation to construct functionalized N-heterocycles, such as spirocyclic- or bicyclic 3H-indoles or benzazepinones.

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Key Words

benzo-fused N-heterocycles, PIFA

ID: J48-Y2020