Coupling Radical Homoallylic Expansions with C-C Fragmentations for the Synthesis of Heteroaromatics: Quinolines from Reactions of o-Alkenylarylisonitriles with Aryl, Alkyl, and Perfluoroalkyl Radicals.
Publication type: Journal Article
Publication date: 2017-04-03
scimago Q2
wos Q1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
PubMed ID:
28357857
Organic Chemistry
Abstract
Selective addition of radicals to isonitriles can be harnessed for initiating reaction cascades designed to overcome the stereoelectronic restrictions on homoallylic ring expansion in alkyne reactions and to develop a new general route for the preparation of N-heteroaromatics. This method utilizes alkenes as synthetic equivalents of alkynes by coupling homoallylic ring expansion to yield the formal "6-endo" products with aromatization via stereoelectronically assisted C-C bond scission. Computational analysis of the homoallyic expansion potential energy surface reveals that the indirect 5-exo/3-exo/retro-3-exo path is faster than the direct 6-endo-trig closure, revealing the general exo-preference for the cyclization processes.
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45
Total citations:
45
Citations from 2024:
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(15.55%)
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Evoniuk C. J. et al. Coupling Radical Homoallylic Expansions with C-C Fragmentations for the Synthesis of Heteroaromatics: Quinolines from Reactions of o-Alkenylarylisonitriles with Aryl, Alkyl, and Perfluoroalkyl Radicals. // Journal of Organic Chemistry. 2017. Vol. 82. No. 8. pp. 4265-4278.
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Evoniuk C. J., Gomes G. D. P., Ly M., White F. D., Alabugin I. V. Coupling Radical Homoallylic Expansions with C-C Fragmentations for the Synthesis of Heteroaromatics: Quinolines from Reactions of o-Alkenylarylisonitriles with Aryl, Alkyl, and Perfluoroalkyl Radicals. // Journal of Organic Chemistry. 2017. Vol. 82. No. 8. pp. 4265-4278.
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RIS
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TY - JOUR
DO - 10.1021/acs.joc.7b00262
UR - https://doi.org/10.1021/acs.joc.7b00262
TI - Coupling Radical Homoallylic Expansions with C-C Fragmentations for the Synthesis of Heteroaromatics: Quinolines from Reactions of o-Alkenylarylisonitriles with Aryl, Alkyl, and Perfluoroalkyl Radicals.
T2 - Journal of Organic Chemistry
AU - Evoniuk, Christopher J
AU - Gomes, Gabriel Dos Passos
AU - Ly, Michelle
AU - White, Frankie D.
AU - Alabugin, Igor V.
PY - 2017
DA - 2017/04/03
PB - American Chemical Society (ACS)
SP - 4265-4278
IS - 8
VL - 82
PMID - 28357857
SN - 0022-3263
SN - 1520-6904
ER -
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BibTex (up to 50 authors)
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@article{2017_Evoniuk,
author = {Christopher J Evoniuk and Gabriel Dos Passos Gomes and Michelle Ly and Frankie D. White and Igor V. Alabugin},
title = {Coupling Radical Homoallylic Expansions with C-C Fragmentations for the Synthesis of Heteroaromatics: Quinolines from Reactions of o-Alkenylarylisonitriles with Aryl, Alkyl, and Perfluoroalkyl Radicals.},
journal = {Journal of Organic Chemistry},
year = {2017},
volume = {82},
publisher = {American Chemical Society (ACS)},
month = {apr},
url = {https://doi.org/10.1021/acs.joc.7b00262},
number = {8},
pages = {4265--4278},
doi = {10.1021/acs.joc.7b00262}
}
Cite this
MLA
Copy
Evoniuk, Christopher J., et al. “Coupling Radical Homoallylic Expansions with C-C Fragmentations for the Synthesis of Heteroaromatics: Quinolines from Reactions of o-Alkenylarylisonitriles with Aryl, Alkyl, and Perfluoroalkyl Radicals..” Journal of Organic Chemistry, vol. 82, no. 8, Apr. 2017, pp. 4265-4278. https://doi.org/10.1021/acs.joc.7b00262.