Green-Light-Driven Fe(III)(btz)3Photocatalysis in the Radical Cationic [4+2] Cycloaddition Reaction

Yu Jeong Jang; Hyeju An; Seunghee Choi; Jayeon Hong; Seung Hyun Lee; Kwang Hyun Ahn; Youngmin You; Eun Joo Kang

doi:10.1021/acs.orglett.2c01779

Green-Light-Driven Fe(III)(btz)₃Photocatalysis in the Radical Cationic [4+2] Cycloaddition Reaction

Yu Jeong Jang, Hyeju An, Seunghee Choi, Jayeon Hong, Seung Hyun Lee, Kwang Hyun Ahn, Youngmin You, Eun Joo Kang

Department of Chemical Engineering & Materials Science

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

19 Scopus citations

Abstract

Green-light-driven Fe^III(btz)₃photocatalysis for the radical cationic [4+2] cycloaddition of terminal styrenes and nucleophilic dienes has been investigated. The Fe-MIC (mesoionic carbene) complex forms a ligand-to-metal charge-transfer transition state with relatively high excited-state reduction potentials that can selectively oxidize terminal styrene derivatives. Unique multisubstituted cyclohexenes and structurally complex biorelevant cyclohexenes were constructed, highlighting the usefulness of this mild and practical first-row transition metal complex system.

Original language	English
Pages (from-to)	4479-4484
Number of pages	6
Journal	Organic Letters
Volume	24
Issue number	24
DOIs	https://doi.org/10.1021/acs.orglett.2c01779
State	Published - 24 Jun 2022

Bibliographical note

Funding Information:
This study was supported by the Ministry of Education, Science and Technology, National Research Foundation (NRF-2021R1A4A1030449, NRF-2021R1A2C1013993, NRF-2015M3D1A1070639, and NRF-2019R1A2C2003969), and the GRRC program of Gyeonggi province [GRRC-kyunghee2017(A01)].

Publisher Copyright:
© 2022 American Chemical Society. All rights reserved.

Access to Document

10.1021/acs.orglett.2c01779

Cite this

@article{195a882aab544c228bd251e64073c206,

title = "Green-Light-Driven Fe(III)(btz)3Photocatalysis in the Radical Cationic [4+2] Cycloaddition Reaction",

abstract = "Green-light-driven FeIII(btz)3photocatalysis for the radical cationic [4+2] cycloaddition of terminal styrenes and nucleophilic dienes has been investigated. The Fe-MIC (mesoionic carbene) complex forms a ligand-to-metal charge-transfer transition state with relatively high excited-state reduction potentials that can selectively oxidize terminal styrene derivatives. Unique multisubstituted cyclohexenes and structurally complex biorelevant cyclohexenes were constructed, highlighting the usefulness of this mild and practical first-row transition metal complex system.",

author = "Jang, {Yu Jeong} and Hyeju An and Seunghee Choi and Jayeon Hong and Lee, {Seung Hyun} and Ahn, {Kwang Hyun} and Youngmin You and Kang, {Eun Joo}",

note = "Funding Information: This study was supported by the Ministry of Education, Science and Technology, National Research Foundation (NRF-2021R1A4A1030449, NRF-2021R1A2C1013993, NRF-2015M3D1A1070639, and NRF-2019R1A2C2003969), and the GRRC program of Gyeonggi province [GRRC-kyunghee2017(A01)]. Publisher Copyright: {\textcopyright} 2022 American Chemical Society. All rights reserved.",

year = "2022",

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doi = "10.1021/acs.orglett.2c01779",

language = "English",

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T1 - Green-Light-Driven Fe(III)(btz)3Photocatalysis in the Radical Cationic [4+2] Cycloaddition Reaction

AU - Jang, Yu Jeong

AU - An, Hyeju

AU - Choi, Seunghee

AU - Hong, Jayeon

AU - Lee, Seung Hyun

AU - Ahn, Kwang Hyun

AU - You, Youngmin

AU - Kang, Eun Joo

N1 - Funding Information: This study was supported by the Ministry of Education, Science and Technology, National Research Foundation (NRF-2021R1A4A1030449, NRF-2021R1A2C1013993, NRF-2015M3D1A1070639, and NRF-2019R1A2C2003969), and the GRRC program of Gyeonggi province [GRRC-kyunghee2017(A01)]. Publisher Copyright: © 2022 American Chemical Society. All rights reserved.

PY - 2022/6/24

Y1 - 2022/6/24

N2 - Green-light-driven FeIII(btz)3photocatalysis for the radical cationic [4+2] cycloaddition of terminal styrenes and nucleophilic dienes has been investigated. The Fe-MIC (mesoionic carbene) complex forms a ligand-to-metal charge-transfer transition state with relatively high excited-state reduction potentials that can selectively oxidize terminal styrene derivatives. Unique multisubstituted cyclohexenes and structurally complex biorelevant cyclohexenes were constructed, highlighting the usefulness of this mild and practical first-row transition metal complex system.

AB - Green-light-driven FeIII(btz)3photocatalysis for the radical cationic [4+2] cycloaddition of terminal styrenes and nucleophilic dienes has been investigated. The Fe-MIC (mesoionic carbene) complex forms a ligand-to-metal charge-transfer transition state with relatively high excited-state reduction potentials that can selectively oxidize terminal styrene derivatives. Unique multisubstituted cyclohexenes and structurally complex biorelevant cyclohexenes were constructed, highlighting the usefulness of this mild and practical first-row transition metal complex system.

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