Endo/Exo-Controllable Photocyclization by EnT-SET-Switch

Xian Peng Cai; Bin Hong Han; Fu Tong Cen; Jian Ping Qu; Yan Biao Kang

doi:10.1021/acs.orglett.3c00837

Endo/Exo-Controllable Photocyclization by EnT-SET-Switch

Xian Peng Cai, Bin Hong Han, Fu Tong Cen, Jian Ping Qu, Yan Biao Kang

School of Chemistry and Moleculai Engineering

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

13 Scopus citations

Abstract

CBZ6, a redox-neutral non-donor-acceptor-type organo-photocatalyst, presents a strong reductive potential with an oxidative potential of −2.16 V (vs SCE). It can work as a photosensitizer for both single-electron transfer and triplet energy transfer processes. This feature enables site-selective control in the intramolecular hydroarylation of acrylamides. Both 5-exo-trig and 6-endo-trig cyclization products could be prepared regiospecfically under mild conditions. No transition metal, halogen-containing reagents, or additional reductant or oxidant is involved. This process provides a concise and environmentally sustainable access to a series of oxindoles and dihydroquinolinones.

Original language	English
Pages (from-to)	2863-2867
Number of pages	5
Journal	Organic Letters
Volume	25
Issue number	16
DOIs	https://doi.org/10.1021/acs.orglett.3c00837
State	Published - 28 Apr 2023

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title = "Endo/Exo-Controllable Photocyclization by EnT-SET-Switch",

abstract = "CBZ6, a redox-neutral non-donor-acceptor-type organo-photocatalyst, presents a strong reductive potential with an oxidative potential of −2.16 V (vs SCE). It can work as a photosensitizer for both single-electron transfer and triplet energy transfer processes. This feature enables site-selective control in the intramolecular hydroarylation of acrylamides. Both 5-exo-trig and 6-endo-trig cyclization products could be prepared regiospecfically under mild conditions. No transition metal, halogen-containing reagents, or additional reductant or oxidant is involved. This process provides a concise and environmentally sustainable access to a series of oxindoles and dihydroquinolinones.",

author = "Cai, {Xian Peng} and Han, {Bin Hong} and Cen, {Fu Tong} and Qu, {Jian Ping} and Kang, {Yan Biao}",

note = "Publisher Copyright: {\textcopyright} 2023 American Chemical Society.",

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doi = "10.1021/acs.orglett.3c00837",

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T1 - Endo/Exo-Controllable Photocyclization by EnT-SET-Switch

AU - Cai, Xian Peng

AU - Han, Bin Hong

AU - Cen, Fu Tong

AU - Qu, Jian Ping

AU - Kang, Yan Biao

PY - 2023/4/28

Y1 - 2023/4/28

N2 - CBZ6, a redox-neutral non-donor-acceptor-type organo-photocatalyst, presents a strong reductive potential with an oxidative potential of −2.16 V (vs SCE). It can work as a photosensitizer for both single-electron transfer and triplet energy transfer processes. This feature enables site-selective control in the intramolecular hydroarylation of acrylamides. Both 5-exo-trig and 6-endo-trig cyclization products could be prepared regiospecfically under mild conditions. No transition metal, halogen-containing reagents, or additional reductant or oxidant is involved. This process provides a concise and environmentally sustainable access to a series of oxindoles and dihydroquinolinones.

AB - CBZ6, a redox-neutral non-donor-acceptor-type organo-photocatalyst, presents a strong reductive potential with an oxidative potential of −2.16 V (vs SCE). It can work as a photosensitizer for both single-electron transfer and triplet energy transfer processes. This feature enables site-selective control in the intramolecular hydroarylation of acrylamides. Both 5-exo-trig and 6-endo-trig cyclization products could be prepared regiospecfically under mild conditions. No transition metal, halogen-containing reagents, or additional reductant or oxidant is involved. This process provides a concise and environmentally sustainable access to a series of oxindoles and dihydroquinolinones.

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DO - 10.1021/acs.orglett.3c00837

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AN - SCOPUS:85154028758

SN - 1523-7060

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SP - 2863

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JO - Organic Letters

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ER -

Endo/Exo-Controllable Photocyclization by EnT-SET-Switch

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