volume 27 issue 1 pages 533-538

Trinuclear Borane (B3H7)-Mediated Selective C4–H Alkylation and Phosphonation of Quinolines and Tetrahydroquinolines

Publication typeJournal Article
Publication date2025-01-01
scimago Q1
wos Q1
SJR1.235
CiteScore8.7
Impact factor5.0
ISSN15237060, 15237052
Abstract
Herein, we report a method for the regioselective alkylation and phosphonation of quinoline C4–H via a B3H7-mediated nucleophilic addition of Turbo Grignard reagents and phosphine oxide anions to quinolines bearing different substituents, affording the 4-alkyl and 4-phosphoryl quinolines and tetrahydroquinolines after one-pot oxidation or reduction. The results indicate that coordination of the B3H7 group can activate substrates toward a potential 1,4-dearomative addition and subtly control the regioselectivity by preventing the 1,2-dearomative addition.
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Pan Q. et al. Trinuclear Borane (B3H7)-Mediated Selective C4–H Alkylation and Phosphonation of Quinolines and Tetrahydroquinolines // Organic Letters. 2025. Vol. 27. No. 1. pp. 533-538.
GOST all authors (up to 50) Copy
Pan Q., Jia S., Fan Z., Cao L., Ma Y., Chen X. Trinuclear Borane (B3H7)-Mediated Selective C4–H Alkylation and Phosphonation of Quinolines and Tetrahydroquinolines // Organic Letters. 2025. Vol. 27. No. 1. pp. 533-538.
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TY - JOUR
DO - 10.1021/acs.orglett.4c04713
UR - https://pubs.acs.org/doi/10.1021/acs.orglett.4c04713
TI - Trinuclear Borane (B3H7)-Mediated Selective C4–H Alkylation and Phosphonation of Quinolines and Tetrahydroquinolines
T2 - Organic Letters
AU - Pan, Qiaojing
AU - Jia, Sihan
AU - Fan, Zi-Heng
AU - Cao, Lei
AU - Ma, Yanna
AU - Chen, Xuenian
PY - 2025
DA - 2025/01/01
PB - American Chemical Society (ACS)
SP - 533-538
IS - 1
VL - 27
PMID - 39743625
SN - 1523-7060
SN - 1523-7052
ER -
BibTex |
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@article{2025_Pan,
author = {Qiaojing Pan and Sihan Jia and Zi-Heng Fan and Lei Cao and Yanna Ma and Xuenian Chen},
title = {Trinuclear Borane (B3H7)-Mediated Selective C4–H Alkylation and Phosphonation of Quinolines and Tetrahydroquinolines},
journal = {Organic Letters},
year = {2025},
volume = {27},
publisher = {American Chemical Society (ACS)},
month = {jan},
url = {https://pubs.acs.org/doi/10.1021/acs.orglett.4c04713},
number = {1},
pages = {533--538},
doi = {10.1021/acs.orglett.4c04713}
}
MLA
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Pan, Qiaojing, et al. “Trinuclear Borane (B3H7)-Mediated Selective C4–H Alkylation and Phosphonation of Quinolines and Tetrahydroquinolines.” Organic Letters, vol. 27, no. 1, Jan. 2025, pp. 533-538. https://pubs.acs.org/doi/10.1021/acs.orglett.4c04713.