Open Access
An enantioconvergent halogenophilic nucleophilic substitution (S N 2X) reaction
Publication type: Journal Article
Publication date: 2019-01-25
scimago Q1
wos Q1
SJR: 10.416
CiteScore: 48.4
Impact factor: 45.8
ISSN: 00368075, 10959203
PubMed ID:
30679372
Multidisciplinary
Abstract
Attack from the front
Biomolecular substitution reactions are widely applied to compounds with carbon-halogen bonds. Typically, an incoming reactive group will attack the carbon from behind its bond with the halogen, causing the halogen to depart in the opposite direction. Zhang et al. now present an asymmetric catalytic substitution reaction that flips the script with an attack on the halogen from the front. Specifically, nitrogen and sulfur nucleophiles stripped bromine from a variety of carbon centers activated by electron-withdrawing groups. A chiral cationic catalyst then directed the carbon fragment back to form a carbon-sulfur or carbon-nitrogen bond enantioselectively.
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Metrics
132
Total citations:
132
Citations from 2024:
37
(28.25%)
Cite this
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GOST
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Zhang X. et al. An enantioconvergent halogenophilic nucleophilic substitution (S N 2X) reaction // Science. 2019. Vol. 363. No. 6425. pp. 400-404.
GOST all authors (up to 50)
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Zhang X., Ren J., Tan S. M., Tan D., Lee R., Tan C. An enantioconvergent halogenophilic nucleophilic substitution (S N 2X) reaction // Science. 2019. Vol. 363. No. 6425. pp. 400-404.
Cite this
RIS
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TY - JOUR
DO - 10.1126/science.aau7797
UR - https://doi.org/10.1126/science.aau7797
TI - An enantioconvergent halogenophilic nucleophilic substitution (S N 2X) reaction
T2 - Science
AU - Zhang, Xin
AU - Ren, Jingyun
AU - Tan, Siu Min
AU - Tan, Davin
AU - Lee, Richmond
AU - Tan, Choon-Hong
PY - 2019
DA - 2019/01/25
PB - American Association for the Advancement of Science (AAAS)
SP - 400-404
IS - 6425
VL - 363
PMID - 30679372
SN - 0036-8075
SN - 1095-9203
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2019_Zhang,
author = {Xin Zhang and Jingyun Ren and Siu Min Tan and Davin Tan and Richmond Lee and Choon-Hong Tan},
title = {An enantioconvergent halogenophilic nucleophilic substitution (S N 2X) reaction},
journal = {Science},
year = {2019},
volume = {363},
publisher = {American Association for the Advancement of Science (AAAS)},
month = {jan},
url = {https://doi.org/10.1126/science.aau7797},
number = {6425},
pages = {400--404},
doi = {10.1126/science.aau7797}
}
Cite this
MLA
Copy
Zhang, Xin, et al. “An enantioconvergent halogenophilic nucleophilic substitution (S N 2X) reaction.” Science, vol. 363, no. 6425, Jan. 2019, pp. 400-404. https://doi.org/10.1126/science.aau7797.