American Chemical Society (ACS)
Journal of Organic Chemistry
,  volume 90 ,  issue 25 ,  pages 8570-8577

Direct C4 Halogenation of Isoquinolines via a Boc2O-Mediated Dearomatization Strategy

Publication type: Journal Article
Publication date: 2025-06-16
American Chemical Society (ACS)
scimago Q2
wos Q1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
Abstract
A cost-effective method for directly halogenating isoquinolines at the C4 position has been developed through a one-pot sequence involving Boc2O-mediated dearomatization, electrophilic halogenation (X = Cl, Br, I), and acid-promoted rearomatization. This reaction exhibited high C4 site selectivity, efficiently affording 4-halogenated isoquinolines, and demonstrated good functional group tolerance at C5-C8. In addition, the C-X bond-containing products could serve as versatile synthetic intermediates for further modification of isoquinolines, including Suzuki coupling, Sonogashira coupling, and Stille coupling.
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Song B. et al. Direct C4 Halogenation of Isoquinolines via a Boc2O-Mediated Dearomatization Strategy // Journal of Organic Chemistry. 2025. Vol. 90. No. 25. pp. 8570-8577.
GOST all authors (up to 50) Copy
Song B., Cai J., Dazhong Y., Xiang F., Zhou J., Han X. L. Direct C4 Halogenation of Isoquinolines via a Boc2O-Mediated Dearomatization Strategy // Journal of Organic Chemistry. 2025. Vol. 90. No. 25. pp. 8570-8577.
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TY - JOUR
DO - 10.1021/acs.joc.5c00535
UR - https://pubs.acs.org/doi/10.1021/acs.joc.5c00535
TI - Direct C4 Halogenation of Isoquinolines via a Boc2O-Mediated Dearomatization Strategy
T2 - Journal of Organic Chemistry
AU - Song, Bingru
AU - Cai, Jiangtao
AU - Dazhong, Yuan
AU - Xiang, Fengjiao
AU - Zhou, Jinming
AU - Han, Xiao Li
PY - 2025
DA - 2025/06/16
PB - American Chemical Society (ACS)
SP - 8570-8577
IS - 25
VL - 90
SN - 0022-3263
SN - 1520-6904
ER -
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@article{2025_Song,
author = {Bingru Song and Jiangtao Cai and Yuan Dazhong and Fengjiao Xiang and Jinming Zhou and Xiao Li Han},
title = {Direct C4 Halogenation of Isoquinolines via a Boc2O-Mediated Dearomatization Strategy},
journal = {Journal of Organic Chemistry},
year = {2025},
volume = {90},
publisher = {American Chemical Society (ACS)},
month = {jun},
url = {https://pubs.acs.org/doi/10.1021/acs.joc.5c00535},
number = {25},
pages = {8570--8577},
doi = {10.1021/acs.joc.5c00535}
}
MLA
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Song, Bingru, et al. “Direct C4 Halogenation of Isoquinolines via a Boc2O-Mediated Dearomatization Strategy.” Journal of Organic Chemistry, vol. 90, no. 25, Jun. 2025, pp. 8570-8577. https://pubs.acs.org/doi/10.1021/acs.joc.5c00535.