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Metal-Free Photoinduced Hydroalkylation Cascade Enabled by an Electron-Donor-Acceptor Complex

preprint
submitted on 28.02.2020 and posted on 28.02.2020 by José Tiago Menezes Correia, Gustavo Piva da Silva, Camila Menezes Kisukuri, Elias André, Bruno Pires, Pablo Silva Carneiro, Marcio Weber Paixão
A metal- and catalyst-free photoinduced radical cascade hydroalkylation of 1,7-enynes has been disclosed. The process is triggered by a SET event involving a photoexcited electron-donor-aceptor complex between NHPI ester and Hantzsch ester, which decomposes to afford a tertiary radical that is readily trapped by the enyne. The method provides an operationally simple, robust and step-economical approach to the construction of diversely functionalized dihydroquinolinones bearing quaternary-centers. A sequential one-pot hydroalkylation-isomerization approach is also allowed giving access to a family of quinolinones. A wide substrate scope and high functional group tolerance was observed in both approaches.

Funding

CNPq (INCT Catálise)

FAPESP 14/50249-8

FAPESP 15/17141-1

FAPESP 17/10015-6

FAPESP 18/12986-1

Coordenação de Aperfeiçoamento de Pessoal de Nível Superior - Brasil (CAPES) - Finance Code 001

GSK

History

Email Address of Submitting Author

josetiago@gmail.com

Institution

Federal University of São Carlos

Country

Brazil

ORCID For Submitting Author

0000-0002-4410-7788

Declaration of Conflict of Interest

No conflict of interest

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