Organic Letters
Organic Letters
5 years ago

Visible-Light-Mediated Addition of Phenacyl Bromides onto Cyclopropenes

Visible-Light-Mediated Addition of Phenacyl Bromides onto Cyclopropenes
Frédéric Robert, Yannick Landais, Ashique Hussain Jatoi, Nitin S. Dange
Visible-light-promoted addition of α-bromoacetophenones onto the cyclopropene π-system in the presence of the fac-Ir(ppy)3 catalyst was shown to afford the corresponding 1(4H)-naphthalenones. The syn-carboarylation of the cyclopropene is followed by a cyclopropane ring opening under the basic conditions, allowing the formation of two C–C bonds and the generation of 1(4H)-naphthalenones bearing an all-carbon benzylic quaternary stereocenter.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b01651

DOI: 10.1021/acs.orglett.7b01651

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