Angewandte Chemie - International Edition, volume 59, issue 9, pages 3385-3398
Uncovering the Neglected Similarities of Arynes and Donor–Acceptor Cyclopropanes
Publication type: Journal Article
Publication date: 2019-12-12
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor: 16.6
ISSN: 14337851, 15213773
PubMed ID:
31529661
General Chemistry
Catalysis
Abstract
Arynes and donor-acceptor (D-A) cyclopropanes are two classes of strained systems having the potential for numerous applications in organic synthesis. The last two decades have witnessed a renaissance of interest in the chemistry of these species primarily because of the mild and robust methods for their generation or activation. Commonly, arynes as easily polarizable systems result in 1,2-disubstitution, whereas D-A cyclopropanes as polarized systems lead to 1,3-bisfunctionalization thereby showing striking similarities. Transformations with 1,2- and 1,3-dipoles afford cyclic structures. With arynes, emerging four-membered rings as intermediates might react further, whereas the analogous five-membered rings obtained from D-A cyclopropanes are most often the final products. However, there are a few cases where these intermediates behave surprisingly differently. This Minireview highlights the parallels in reactivity between arynes and D-A cyclopropanes thereby shedding light on the neglected similarities of these two reactive species.
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Werz D. B., Biju A. Uncovering the Neglected Similarities of Arynes and Donor–Acceptor Cyclopropanes // Angewandte Chemie - International Edition. 2019. Vol. 59. No. 9. pp. 3385-3398.
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Werz D. B., Biju A. Uncovering the Neglected Similarities of Arynes and Donor–Acceptor Cyclopropanes // Angewandte Chemie - International Edition. 2019. Vol. 59. No. 9. pp. 3385-3398.
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TY - JOUR
DO - 10.1002/anie.201909213
UR - https://doi.org/10.1002/anie.201909213
TI - Uncovering the Neglected Similarities of Arynes and Donor–Acceptor Cyclopropanes
T2 - Angewandte Chemie - International Edition
AU - Werz, Daniel B.
AU - Biju, A.T
PY - 2019
DA - 2019/12/12 00:00:00
PB - Wiley
SP - 3385-3398
IS - 9
VL - 59
PMID - 31529661
SN - 1433-7851
SN - 1521-3773
ER -
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@article{2019_Werz,
author = {Daniel B. Werz and A.T Biju},
title = {Uncovering the Neglected Similarities of Arynes and Donor–Acceptor Cyclopropanes},
journal = {Angewandte Chemie - International Edition},
year = {2019},
volume = {59},
publisher = {Wiley},
month = {dec},
url = {https://doi.org/10.1002/anie.201909213},
number = {9},
pages = {3385--3398},
doi = {10.1002/anie.201909213}
}
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Werz, Daniel B., and A.T Biju. “Uncovering the Neglected Similarities of Arynes and Donor–Acceptor Cyclopropanes.” Angewandte Chemie - International Edition, vol. 59, no. 9, Dec. 2019, pp. 3385-3398. https://doi.org/10.1002/anie.201909213.