Cyclopropenes for the Stepwise Synthesis of 1,2,4,5-Tetraarylbenzenes via 1,4-Cyclohexadienes

[Image: see text] This paper describes a synthetic approach to the synthesis of 1,2,4,5-tetraarylbenzene derivatives from cyclopropenes. The Lewis acid-mediated dimerization of cyclopropenes gives tricyclo[3.1.0.0(2,4)]hexane derivatives. The subsequent thermal ring-opening reaction under solvent-fr...

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Detalles Bibliográficos
Autores principales: Kishida, Satoshi, Takano, Misaki, Sekiya, Takuya, Ukaji, Yutaka, Endo, Kohei
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9639005/
https://www.ncbi.nlm.nih.gov/pubmed/36201259
http://dx.doi.org/10.1021/acs.joc.2c01261
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author Kishida, Satoshi
Takano, Misaki
Sekiya, Takuya
Ukaji, Yutaka
Endo, Kohei
author_facet Kishida, Satoshi
Takano, Misaki
Sekiya, Takuya
Ukaji, Yutaka
Endo, Kohei
author_sort Kishida, Satoshi
collection PubMed
description [Image: see text] This paper describes a synthetic approach to the synthesis of 1,2,4,5-tetraarylbenzene derivatives from cyclopropenes. The Lewis acid-mediated dimerization of cyclopropenes gives tricyclo[3.1.0.0(2,4)]hexane derivatives. The subsequent thermal ring-opening reaction under solvent-free conditions gives 1,4-cyclohexadienes bearing quaternary carbons. The novel Br(2)-mediated oxidative rearrangement of 1,4-cyclohexadienes takes place to give 1,2,4,5-tetraarylbenzene derivatives in high to excellent yields.
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spelling pubmed-96390052022-11-08 Cyclopropenes for the Stepwise Synthesis of 1,2,4,5-Tetraarylbenzenes via 1,4-Cyclohexadienes Kishida, Satoshi Takano, Misaki Sekiya, Takuya Ukaji, Yutaka Endo, Kohei J Org Chem [Image: see text] This paper describes a synthetic approach to the synthesis of 1,2,4,5-tetraarylbenzene derivatives from cyclopropenes. The Lewis acid-mediated dimerization of cyclopropenes gives tricyclo[3.1.0.0(2,4)]hexane derivatives. The subsequent thermal ring-opening reaction under solvent-free conditions gives 1,4-cyclohexadienes bearing quaternary carbons. The novel Br(2)-mediated oxidative rearrangement of 1,4-cyclohexadienes takes place to give 1,2,4,5-tetraarylbenzene derivatives in high to excellent yields. American Chemical Society 2022-10-06 2022-11-04 /pmc/articles/PMC9639005/ /pubmed/36201259 http://dx.doi.org/10.1021/acs.joc.2c01261 Text en © 2022 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Kishida, Satoshi
Takano, Misaki
Sekiya, Takuya
Ukaji, Yutaka
Endo, Kohei
Cyclopropenes for the Stepwise Synthesis of 1,2,4,5-Tetraarylbenzenes via 1,4-Cyclohexadienes
title Cyclopropenes for the Stepwise Synthesis of 1,2,4,5-Tetraarylbenzenes via 1,4-Cyclohexadienes
title_full Cyclopropenes for the Stepwise Synthesis of 1,2,4,5-Tetraarylbenzenes via 1,4-Cyclohexadienes
title_fullStr Cyclopropenes for the Stepwise Synthesis of 1,2,4,5-Tetraarylbenzenes via 1,4-Cyclohexadienes
title_full_unstemmed Cyclopropenes for the Stepwise Synthesis of 1,2,4,5-Tetraarylbenzenes via 1,4-Cyclohexadienes
title_short Cyclopropenes for the Stepwise Synthesis of 1,2,4,5-Tetraarylbenzenes via 1,4-Cyclohexadienes
title_sort cyclopropenes for the stepwise synthesis of 1,2,4,5-tetraarylbenzenes via 1,4-cyclohexadienes
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9639005/
https://www.ncbi.nlm.nih.gov/pubmed/36201259
http://dx.doi.org/10.1021/acs.joc.2c01261
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