Protonation-Enhanced Reactivity of Triplet State in Dearomative Photocycloaddition of Quinolines to Olefins

Tatsuya Morofuji; Shota Nagai; Youhei Chitose; Manabu Abe; Naokazu Kano

doi:10.1021/acs.orglett.1c02026

Protonation-Enhanced Reactivity of Triplet State in Dearomative Photocycloaddition of Quinolines to Olefins

Tatsuya Morofuji, Shota Nagai, Youhei Chitose, Manabu Abe, Naokazu Kano

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

12 Citations (Scopus)

Abstract

The intermolecular dearomative cycloaddition of acidified bicyclic azaarenes with olefins was recently reported. We report here the crucial role of the acid in the dearomative photocycloaddition of quinolines to olefins. Experimental and theoretical results show that the key role of the protonation of quinolines is not to promote the energy transfer but to enhance the reactivity of the triplet state of quinolines toward olefins.

Original language	English
Pages (from-to)	6257-6261
Number of pages	5
Journal	Organic letters
Volume	23
Issue number	16
DOIs	https://doi.org/10.1021/acs.orglett.1c02026
Publication status	Published - Aug 20 2021
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.1c02026

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title = "Protonation-Enhanced Reactivity of Triplet State in Dearomative Photocycloaddition of Quinolines to Olefins",

abstract = "The intermolecular dearomative cycloaddition of acidified bicyclic azaarenes with olefins was recently reported. We report here the crucial role of the acid in the dearomative photocycloaddition of quinolines to olefins. Experimental and theoretical results show that the key role of the protonation of quinolines is not to promote the energy transfer but to enhance the reactivity of the triplet state of quinolines toward olefins. ",

author = "Tatsuya Morofuji and Shota Nagai and Youhei Chitose and Manabu Abe and Naokazu Kano",

note = "Funding Information: This research was partially supported by a MEXT-supported program for Strategic Research Foundations at Private Universities, JSPS KAKENHI grant numbers JP19K15570 (T.M.), JP18J20500 (Y.C.), and JP21H01921 (M.A.), JST CREST (grant number JPMJCR18R4) (M.A.), and the Asahi Glass Foundation (T.M.). DFT calculations were performed using the Research Center for Computational Science, Okazaki, Japan. Publisher Copyright: {\textcopyright} 2021 American Chemical Society.",

year = "2021",

month = aug,

day = "20",

doi = "10.1021/acs.orglett.1c02026",

language = "English",

volume = "23",

pages = "6257--6261",

journal = "Organic Letters",

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T1 - Protonation-Enhanced Reactivity of Triplet State in Dearomative Photocycloaddition of Quinolines to Olefins

AU - Morofuji, Tatsuya

AU - Nagai, Shota

AU - Chitose, Youhei

AU - Abe, Manabu

AU - Kano, Naokazu

N1 - Funding Information: This research was partially supported by a MEXT-supported program for Strategic Research Foundations at Private Universities, JSPS KAKENHI grant numbers JP19K15570 (T.M.), JP18J20500 (Y.C.), and JP21H01921 (M.A.), JST CREST (grant number JPMJCR18R4) (M.A.), and the Asahi Glass Foundation (T.M.). DFT calculations were performed using the Research Center for Computational Science, Okazaki, Japan. Publisher Copyright: © 2021 American Chemical Society.

PY - 2021/8/20

Y1 - 2021/8/20

N2 - The intermolecular dearomative cycloaddition of acidified bicyclic azaarenes with olefins was recently reported. We report here the crucial role of the acid in the dearomative photocycloaddition of quinolines to olefins. Experimental and theoretical results show that the key role of the protonation of quinolines is not to promote the energy transfer but to enhance the reactivity of the triplet state of quinolines toward olefins.

AB - The intermolecular dearomative cycloaddition of acidified bicyclic azaarenes with olefins was recently reported. We report here the crucial role of the acid in the dearomative photocycloaddition of quinolines to olefins. Experimental and theoretical results show that the key role of the protonation of quinolines is not to promote the energy transfer but to enhance the reactivity of the triplet state of quinolines toward olefins.

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Protonation-Enhanced Reactivity of Triplet State in Dearomative Photocycloaddition of Quinolines to Olefins

Abstract

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