Conformer-related pathways in cycloaddition of vinylaziridines and alkynes catalyzed by rhodium(I)-complex

Jian Chen; Minmin Huang; Fei Xia

doi:10.1016/j.cplett.2018.10.011

Conformer-related pathways in cycloaddition of vinylaziridines and alkynes catalyzed by rhodium(I)-complex

Jian Chen
, Minmin Huang
, Fei Xia^*

^*Corresponding author for this work

School of Chemistry and Molecular Engineering

East China Normal University

Research output: Contribution to journal › Article › peer-review

2 Scopus citations

Abstract

The conformer-related reaction pathways in the cycloaddition of vinylaziridines with alkynes were calculated using DFT methods. The calculated results reveal that the ring-opening products of vinylaziridines possess two different conformers with the specific sites available for coordination of alkynes. The formed alkyne-coordinated complexes results in the different C–N bond addition intermediates. In the cycloaddition reaction catalyzed by [Rh(η⁶-C₁₀H₈)(COD)]SbF₆, the intermediate needs an isomerization to yield the final [5 + 2] cycloaddition product. In the reaction catalyzed by [Rh(NBD)₂]BF₄, such an isomerization is dispensable to yield the final [3 + 2] cycloaddition product.

Original language	English
Pages (from-to)	21-25
Number of pages	5
Journal	Chemical Physics Letters
Volume	713
DOIs	https://doi.org/10.1016/j.cplett.2018.10.011
State	Published - Dec 2018

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title = "Conformer-related pathways in cycloaddition of vinylaziridines and alkynes catalyzed by rhodium(I)-complex",

abstract = "The conformer-related reaction pathways in the cycloaddition of vinylaziridines with alkynes were calculated using DFT methods. The calculated results reveal that the ring-opening products of vinylaziridines possess two different conformers with the specific sites available for coordination of alkynes. The formed alkyne-coordinated complexes results in the different C–N bond addition intermediates. In the cycloaddition reaction catalyzed by [Rh(η6-C10H8)(COD)]SbF6, the intermediate needs an isomerization to yield the final [5 + 2] cycloaddition product. In the reaction catalyzed by [Rh(NBD)2]BF4, such an isomerization is dispensable to yield the final [3 + 2] cycloaddition product.",

author = "Jian Chen and Minmin Huang and Fei Xia",

note = "Publisher Copyright: {\textcopyright} 2018",

year = "2018",

month = dec,

doi = "10.1016/j.cplett.2018.10.011",

language = "英语",

volume = "713",

pages = "21--25",

journal = "Chemical Physics Letters",

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T1 - Conformer-related pathways in cycloaddition of vinylaziridines and alkynes catalyzed by rhodium(I)-complex

AU - Chen, Jian

AU - Huang, Minmin

AU - Xia, Fei

PY - 2018/12

Y1 - 2018/12

N2 - The conformer-related reaction pathways in the cycloaddition of vinylaziridines with alkynes were calculated using DFT methods. The calculated results reveal that the ring-opening products of vinylaziridines possess two different conformers with the specific sites available for coordination of alkynes. The formed alkyne-coordinated complexes results in the different C–N bond addition intermediates. In the cycloaddition reaction catalyzed by [Rh(η6-C10H8)(COD)]SbF6, the intermediate needs an isomerization to yield the final [5 + 2] cycloaddition product. In the reaction catalyzed by [Rh(NBD)2]BF4, such an isomerization is dispensable to yield the final [3 + 2] cycloaddition product.

AB - The conformer-related reaction pathways in the cycloaddition of vinylaziridines with alkynes were calculated using DFT methods. The calculated results reveal that the ring-opening products of vinylaziridines possess two different conformers with the specific sites available for coordination of alkynes. The formed alkyne-coordinated complexes results in the different C–N bond addition intermediates. In the cycloaddition reaction catalyzed by [Rh(η6-C10H8)(COD)]SbF6, the intermediate needs an isomerization to yield the final [5 + 2] cycloaddition product. In the reaction catalyzed by [Rh(NBD)2]BF4, such an isomerization is dispensable to yield the final [3 + 2] cycloaddition product.

UR - https://www.scopus.com/pages/publications/85054460639

U2 - 10.1016/j.cplett.2018.10.011

DO - 10.1016/j.cplett.2018.10.011

M3 - 文章

AN - SCOPUS:85054460639

SN - 0009-2614

VL - 713

SP - 21

EP - 25

JO - Chemical Physics Letters

JF - Chemical Physics Letters

ER -

Conformer-related pathways in cycloaddition of vinylaziridines and alkynes catalyzed by rhodium(I)-complex

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