Keywords
arylacrylamides
carboazidation
indolin-2-ones
N3-Togni reagent
photocatalysis.
radical cyclization
Abstract
Intramolecular carboazidation of N-arylacrylamides with 1-azido-1λ3-benzo[d][1,2]iodaoxol-3(1H)-one (the N3-Togni reagent) affording 3-(azidomethyl)indolin-2-ones proceeds at room temperature under visible light irradiation with 2,4,5,6-tetra(carbazol-9-yl)-1,3-dicyanobenzene assistance. The latter provides the formation of azido radicals from the N3-Togni reagent. The investigated substrate scope involves 12 examples.
References
.
Bräse S., Gil C., Knepper K., Zimmermann V.
Angewandte Chemie - International Edition,
2005
.
Thirumurugan P., Matosiuk D., Jozwiak K.
Chemical Reviews,
2013
.
Kaur M., Singh M., Chadha N., Silakari O.
European Journal of Medicinal Chemistry,
2016
.
Marchese A.D., Larin E.M., Mirabi B., Lautens M.
Accounts of Chemical Research,
2020
.
.
Zard S.Z.
Chemical Society Reviews,
2008
.
Matcha K., Narayan R., Antonchick A.P.
Angewandte Chemie - International Edition,
2013
.
Wei X., Li Y., Zhou A., Yang T., Yang S.
Organic Letters,
2013
.
Liu Z., Liu Z.
Organic Letters,
2017
.
Chan C., Xing Q., Chow Y., Hung S., Yu W.
Organic Letters,
2019
.
Maiti D., Mahanty K., De Sarkar S.
Chemistry - An Asian Journal,
2021
.
Qiu J., Zhang R.
Organic and Biomolecular Chemistry,
2014
.
Zhao D., Kang K., Wan W., Jiang H., Deng H., Chen Y., Hao J.
Organic Chemistry Frontiers,
2017
.
Song W., Kozhushkov S.I., Ackermann L.
Angewandte Chemie - International Edition,
2013
.
Yuan Y., Shen T., Wang K., Jiao N.
Chemistry - An Asian Journal,
2013
.
Kong W., Merino E., Nevado C.
Angewandte Chemie - International Edition,
2014
.
Pei C., Liu Y., Chen X., Li J., Zou D., Wu Y., Wu Y.
Advanced Synthesis and Catalysis,
2023