Visible-Light-Induced ortho-Quinone Methides Formation in Situ Using ortho-Alkylarenols as Precursors for Tandem [4 + 2] Cycloaddition Reaction
Тип публикации: Journal Article
Дата публикации: 2024-12-26
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CiteScore: 7.7
Impact factor: 4.7
ISSN: 15237060, 15237052
PubMed ID:
39723814
Краткое описание
Reported herein is the generation of ortho-quinone methides (o-QMs) via metal-free visible-light-induced oxidation of ortho-alkylarenols, as well as their subsequent reaction with olefins to afford chromans in good to excellent yields (up to 91%). The key is the selective activation of the benzylic C(sp3)–H bond of ortho-alkylarenols via single electron transfer (SET) and the formation of o-QMs via hydrogen atom transfer (HAT).
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Shu W. et al. Visible-Light-Induced ortho-Quinone Methides Formation in Situ Using ortho-Alkylarenols as Precursors for Tandem [4 + 2] Cycloaddition Reaction // Organic Letters. 2024. Vol. 27. No. 1. pp. 470-475.
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Shu W. et al. Visible-Light-Induced ortho-Quinone Methides Formation in Situ Using ortho-Alkylarenols as Precursors for Tandem [4 + 2] Cycloaddition Reaction // Organic Letters. 2024. Vol. 27. No. 1. pp. 470-475.
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TY - JOUR
DO - 10.1021/acs.orglett.4c04494
UR - https://pubs.acs.org/doi/10.1021/acs.orglett.4c04494
TI - Visible-Light-Induced ortho-Quinone Methides Formation in Situ Using ortho-Alkylarenols as Precursors for Tandem [4 + 2] Cycloaddition Reaction
T2 - Organic Letters
AU - Shu, Wang
AU - Liang Ge
AU - Ge, Liang
AU - Wang, Cheng
AU - Wang, Chen-hong
AU - Wang, Chenhong
AU - Huang, Zhiyuan
AU - Tung, Chen-Ho
AU - Wu, Li-Zhu
PY - 2024
DA - 2024/12/26
PB - American Chemical Society (ACS)
SP - 470-475
IS - 1
VL - 27
PMID - 39723814
SN - 1523-7060
SN - 1523-7052
ER -
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@article{2024_Shu,
author = {Wang Shu and Liang Ge and Liang Ge and Cheng Wang and Chen-hong Wang and Chenhong Wang and Zhiyuan Huang and Chen-Ho Tung and Li-Zhu Wu and others},
title = {Visible-Light-Induced ortho-Quinone Methides Formation in Situ Using ortho-Alkylarenols as Precursors for Tandem [4 + 2] Cycloaddition Reaction},
journal = {Organic Letters},
year = {2024},
volume = {27},
publisher = {American Chemical Society (ACS)},
month = {dec},
url = {https://pubs.acs.org/doi/10.1021/acs.orglett.4c04494},
number = {1},
pages = {470--475},
doi = {10.1021/acs.orglett.4c04494}
}
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Shu, Wang, et al. “Visible-Light-Induced ortho-Quinone Methides Formation in Situ Using ortho-Alkylarenols as Precursors for Tandem [4 + 2] Cycloaddition Reaction.” Organic Letters, vol. 27, no. 1, Dec. 2024, pp. 470-475. https://pubs.acs.org/doi/10.1021/acs.orglett.4c04494.
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