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

preprint
submitted on 28.02.2020, 06:09 and posted on 28.02.2020, 13:46 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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