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Strain and stereoelectronics in cycloalkyne click chemistry

Trevor Michael Harris 1
Trevor Michael Harris
, 
Igor Vladimirovich Alabugin 2
Igor Vladimirovich Alabugin
10.1016/j.mencom.2019.05.001
Published 2019-04-26
Focus article , Volume 29, Issue 3, 237-248
53
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Harris T. M., Alabugin I. V. Strain and stereoelectronics in cycloalkyne click chemistry // Mendeleev Communications. 2019. Vol. 29. No. 3. pp. 237-248.
GOST all authors (up to 50) Copy
Harris T. M., Alabugin I. V. Strain and stereoelectronics in cycloalkyne click chemistry // Mendeleev Communications. 2019. Vol. 29. No. 3. pp. 237-248.
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TY - JOUR
DO - 10.1016/j.mencom.2019.05.001
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2019.05.001
TI - Strain and stereoelectronics in cycloalkyne click chemistry
T2 - Mendeleev Communications
AU - Harris, Trevor Michael
AU - Alabugin, Igor Vladimirovich
PY - 2019
DA - 2019/04/26
PB - Mendeleev Communications
SP - 237-248
IS - 3
VL - 29
ER -
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@article{2019_Harris,
author = {Trevor Michael Harris and Igor Vladimirovich Alabugin},
title = {Strain and stereoelectronics in cycloalkyne click chemistry},
journal = {Mendeleev Communications},
year = {2019},
volume = {29},
publisher = {Mendeleev Communications},
month = {Apr},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2019.05.001},
number = {3},
pages = {237--248},
doi = {10.1016/j.mencom.2019.05.001}
}
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Harris, Trevor Michael, and Igor Vladimirovich Alabugin. “Strain and stereoelectronics in cycloalkyne click chemistry.” Mendeleev Communications, vol. 29, no. 3, Apr. 2019, pp. 237-248. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2019.05.001.
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Abstract

Due to the broad interest to cycloalkynes in metal-free click chemistry, we present a focused review summarizing current approaches to structural and electronic modifications of cycloalkynes. We illustrate how the combination of reactant destabilization and transition state stabilization can lead to the design of more reactive cycloalkynes that are, paradoxically, less strained. We discuss the concept of ring strain in cycloalkynes and show that increased ring strain does not always equate to increased click reactivity. We summarize direct and remote electronic effects that can be used to enhance click reactivity in cycloalkynes and show how inclusion of transition state stabilizing stereoelectronic effects is essential for the rational design of the cycloalkyne click reagents.

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