Visible-Light-Mediated Addition of Phenacyl Bromides onto Cyclopropenes | Zendy

Nitin S. Dange | Zendy; Ashique Hussain Jatoi | Zendy; Frédéric Robert | Zendy; Yannick Landais | Zendy

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Visible-Light-Mediated Addition of Phenacyl Bromides onto Cyclopropenes

Author(s) -

Nitin S. Dange,

Ashique Hussain Jatoi,

Frédéric Robert,

Yannick Landais

Publication year - 2017

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/acs.orglett.7b01651

Subject(s) - cyclopropene , stereocenter , chemistry , phenacyl , cyclopropane , ring (chemistry) , catalysis , photochemistry , visible spectrum , allene , medicinal chemistry , organic chemistry , enantioselective synthesis , physics , optoelectronics

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.

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