Gold-Catalyzed Nitrene Transfer from Benzofuroxans to N-Allylynamides: Synthesis of 3-Azabicyclo[3.1.0]hexanes.
Publication type: Journal Article
Publication date: 2021-09-02
scimago Q2
wos Q1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
PubMed ID:
34472847
Organic Chemistry
Abstract
The gold-catalyzed reaction between benzofuroxans, functioning as nitrene transfer reagents, and N-allylynamides leads to 3-azabicyclo[3.1.0]hexan-2-imines. This highly selective annulation proceeds smoothly under mild conditions (5 mol % Ph3PAuNTf2, PhCl, 60 °C) and exhibits high functional group tolerance (21 examples, ≤96% yields). The obtained cyclopropanated products represent a useful synthetic platform with an easily modulated substitution pattern as illustrated by their postmodifications. Intramolecular cyclopropanation of gold α-imino carbene intermediates is suggested as a key step of the catalytic cycle.
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Total citations:
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Citations from 2024:
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(35%)
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Shcherbakov N. V. et al. Gold-Catalyzed Nitrene Transfer from Benzofuroxans to N-Allylynamides: Synthesis of 3-Azabicyclo[3.1.0]hexanes. // Journal of Organic Chemistry. 2021. Vol. 86. No. 18. pp. 12964-12972.
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Shcherbakov N. V., Dar’in D., Kukushkin V. Y., Dubovtsev A. Yu. Gold-Catalyzed Nitrene Transfer from Benzofuroxans to N-Allylynamides: Synthesis of 3-Azabicyclo[3.1.0]hexanes. // Journal of Organic Chemistry. 2021. Vol. 86. No. 18. pp. 12964-12972.
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TY - JOUR
DO - 10.1021/acs.joc.1c01654
UR - https://doi.org/10.1021/acs.joc.1c01654
TI - Gold-Catalyzed Nitrene Transfer from Benzofuroxans to N-Allylynamides: Synthesis of 3-Azabicyclo[3.1.0]hexanes.
T2 - Journal of Organic Chemistry
AU - Shcherbakov, Nikolay V
AU - Dar’in, Dmitry
AU - Kukushkin, Vadim Yu.
AU - Dubovtsev, Alexey Yu
PY - 2021
DA - 2021/09/02
PB - American Chemical Society (ACS)
SP - 12964-12972
IS - 18
VL - 86
PMID - 34472847
SN - 0022-3263
SN - 1520-6904
ER -
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@article{2021_Shcherbakov,
author = {Nikolay V Shcherbakov and Dmitry Dar’in and Vadim Yu. Kukushkin and Alexey Yu Dubovtsev},
title = {Gold-Catalyzed Nitrene Transfer from Benzofuroxans to N-Allylynamides: Synthesis of 3-Azabicyclo[3.1.0]hexanes.},
journal = {Journal of Organic Chemistry},
year = {2021},
volume = {86},
publisher = {American Chemical Society (ACS)},
month = {sep},
url = {https://doi.org/10.1021/acs.joc.1c01654},
number = {18},
pages = {12964--12972},
doi = {10.1021/acs.joc.1c01654}
}
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MLA
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Shcherbakov, Nikolay V., et al. “Gold-Catalyzed Nitrene Transfer from Benzofuroxans to N-Allylynamides: Synthesis of 3-Azabicyclo[3.1.0]hexanes..” Journal of Organic Chemistry, vol. 86, no. 18, Sep. 2021, pp. 12964-12972. https://doi.org/10.1021/acs.joc.1c01654.
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