Tandem cyclohexen-3-yne and 1,2,3-cyclohexatriene reactions.
- 1School of Chemistry and Chemical Engineering, Chongqing University, Chongqing, PR China.
- 2School of Chemistry and Chemical Engineering, Chongqing University, Chongqing, PR China. [email protected].
- 3School of Chemistry and Chemical Engineering, Chongqing University, Chongqing, PR China. [email protected].
Abstract
There are three classes of neutral 6-membered reactive species, namely didehydrobenzene (benzyne (1)), dihydrobenzenes (cyclohexyne (2) and 1,2-cyclohexadiene (3)), and benzene isomers (cyclohexen-3-yne (4), 1,2,3-cyclohexatriene (5), and 1,2,4-cyclohexatriene (6)). Although intermediates 1-3 have found broad synthetic applications, the benzene isomers 4-6 received only sporadic attention. To further explore their synthetic utility and, more importantly, to uncover their potential in preparing polysubstituted 1,3-cyclohexadienes, we successfully incorporate cyclohexen-3-yne and 1,2,3-cyclohexatriene into several cascade transformations, such as 1,3-diamination, nucleophilic addition-ene reaction, and nucleophilic addition-[4+2] cycloaddition reaction. Additionally, a 1,5-sulfonyl group migration could occur to deliver a sulfone to the C4-position of the 1,3-cyclohexadiene framework. As a result, a series of 1,2-disubstituted, 1,2,3-trisubstituted, 1,2,4-trisubstituted, and 1,2,3,4-tetrasubstituted 1,3-cyclohexadienes bearing polycyclic ring systems can be efficiently prepared. This study offers a distinctive perspective on these aspects of reactive benzene isomers.
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BibTeX
@article{yin2026tandem,
title = {{Tandem cyclohexen-3-yne and 1,2,3-cyclohexatriene reactions.}},
author = {Wenhao Yin and Ranran Xia and Li Xu and Lianggui Li and Yang Li},
journal = {Nature communications},
year = {2026},
month = sep,
doi = {10.1038/s41467-026-77981-4},
url = {https://europepmc.org/article/MED/42907463},
note = {CC BY-NC-ND},
}
RIS
TY - JOUR
TI - Tandem cyclohexen-3-yne and 1,2,3-cyclohexatriene reactions.
AU - Wenhao Yin
AU - Ranran Xia
AU - Li Xu
AU - Lianggui Li
AU - Yang Li
PY - 2026
DA - 2026/09/21
JO - Nature communications
DO - 10.1038/s41467-026-77981-4
UR - https://europepmc.org/article/MED/42907463
AB - There are three classes of neutral 6-membered reactive species, namely didehydrobenzene (benzyne (1)), dihydrobenzenes (cyclohexyne (2) and 1,2-cyclohexadiene (3)), and benzene isomers (cyclohexen-3-yne (4), 1,2,3-cyclohexatriene (5), and 1,2,4-cyclohexatriene (6)). Although intermediates 1-3 have found broad synthetic applications, the benzene isomers 4-6 received only sporadic attention. To further explore their synthetic utility and, more importantly, to uncover their potential in preparing polysubstituted 1,3-cyclohexadienes, we successfully incorporate cyclohexen-3-yne and 1,2,3-cyclohexatriene into several cascade transformations, such as 1,3-diamination, nucleophilic addition-ene reaction, and nucleophilic addition-[4+2] cycloaddition reaction. Additionally, a 1,5-sulfonyl group migration could occur to deliver a sulfone to the C4-position of the 1,3-cyclohexadiene framework. As a result, a series of 1,2-disubstituted, 1,2,3-trisubstituted, 1,2,4-trisubstituted, and 1,2,3,4-tetrasubstituted 1,3-cyclohexadienes bearing polycyclic ring systems can be efficiently prepared. This study offers a distinctive perspective on these aspects of reactive benzene isomers.
SN - 2041-1723
ER -