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

35 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

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© 2022 American Chemical Society. All rights reserved.

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10.1021/acs.orglett.2c01779

Cite this

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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\}",

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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

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.

UR - https://www.scopus.com/pages/publications/85133100958

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DO - 10.1021/acs.orglett.2c01779

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VL - 24

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JO - Organic Letters

JF - Organic Letters

IS - 24