Visible-Light-Induced Trifluoromethylation of Unactivated Alkenes with Tri(9-anthryl)borane as an Organophotocatalyst

Jisu Moon; Yu Kyung Moon; Do Dam Park; Sukyung Choi; Youngmin You; Eun Jin Cho

doi:10.1021/acs.joc.9b01624

Visible-Light-Induced Trifluoromethylation of Unactivated Alkenes with Tri(9-anthryl)borane as an Organophotocatalyst

Jisu Moon, Yu Kyung Moon, Do Dam Park, Sukyung Choi, Youngmin You, Eun Jin Cho

Chemical Engineering & Materials Science

Research output: Contribution to journal › Article › peer-review

29 Scopus citations

Abstract

Tri(9-anthryl)borane was successfully applied as an organophotocatalyst for the visible-light-induced trifluoromethylation of unactivated alkenes with CF₃I. The mild reaction conditions tolerated a variety of functional groups, and the reaction could be extended to perfluoroalkylations with C₃F₇I and C₄F₉I. Mechanistic studies revealed that the photoredox catalysis involves an oxidative quenching pathway.

Original language	English
Pages (from-to)	12925-12932
Number of pages	8
Journal	Journal of Organic Chemistry
Volume	84
Issue number	20
DOIs	https://doi.org/10.1021/acs.joc.9b01624
State	Published - 18 Oct 2019

Bibliographical note

Funding Information:
We gratefully acknowledge the support from National Research Foundation of Korea for Y.Y. (NRF-2015M3D1A1070639, NRF-2019R1A2C2003969) and E.J.C. (NRF-2012M3A7B4049657, NRF-2014011165, NRF-2017R1A2B2004082).

Publisher Copyright:
© 2019 American Chemical Society.

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10.1021/acs.joc.9b01624

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title = "Visible-Light-Induced Trifluoromethylation of Unactivated Alkenes with Tri(9-anthryl)borane as an Organophotocatalyst",

abstract = "Tri(9-anthryl)borane was successfully applied as an organophotocatalyst for the visible-light-induced trifluoromethylation of unactivated alkenes with CF3I. The mild reaction conditions tolerated a variety of functional groups, and the reaction could be extended to perfluoroalkylations with C3F7I and C4F9I. Mechanistic studies revealed that the photoredox catalysis involves an oxidative quenching pathway.",

author = "Jisu Moon and Moon, {Yu Kyung} and Park, {Do Dam} and Sukyung Choi and Youngmin You and Cho, {Eun Jin}",

note = "Funding Information: We gratefully acknowledge the support from National Research Foundation of Korea for Y.Y. (NRF-2015M3D1A1070639, NRF-2019R1A2C2003969) and E.J.C. (NRF-2012M3A7B4049657, NRF-2014011165, NRF-2017R1A2B2004082). Publisher Copyright: {\textcopyright} 2019 American Chemical Society.",

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AU - Moon, Jisu

AU - Moon, Yu Kyung

AU - Park, Do Dam

AU - Choi, Sukyung

AU - You, Youngmin

AU - Cho, Eun Jin

N1 - Funding Information: We gratefully acknowledge the support from National Research Foundation of Korea for Y.Y. (NRF-2015M3D1A1070639, NRF-2019R1A2C2003969) and E.J.C. (NRF-2012M3A7B4049657, NRF-2014011165, NRF-2017R1A2B2004082). Publisher Copyright: © 2019 American Chemical Society.

PY - 2019/10/18

Y1 - 2019/10/18

N2 - Tri(9-anthryl)borane was successfully applied as an organophotocatalyst for the visible-light-induced trifluoromethylation of unactivated alkenes with CF3I. The mild reaction conditions tolerated a variety of functional groups, and the reaction could be extended to perfluoroalkylations with C3F7I and C4F9I. Mechanistic studies revealed that the photoredox catalysis involves an oxidative quenching pathway.

AB - Tri(9-anthryl)borane was successfully applied as an organophotocatalyst for the visible-light-induced trifluoromethylation of unactivated alkenes with CF3I. The mild reaction conditions tolerated a variety of functional groups, and the reaction could be extended to perfluoroalkylations with C3F7I and C4F9I. Mechanistic studies revealed that the photoredox catalysis involves an oxidative quenching pathway.

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Visible-Light-Induced Trifluoromethylation of Unactivated Alkenes with Tri(9-anthryl)borane as an Organophotocatalyst

Abstract

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