Cargando…
Oxidative coupling of sp(2) and sp(3) carbon–hydrogen bonds to construct dihydrobenzofurans
Metal-catalyzed cross-couplings provide powerful, concise, and accurate methods to construct carbon–carbon bonds from organohalides and organometallic reagents. Recent developments extended cross-couplings to reactions where one of the two partners connects with an aryl or alkyl carbon–hydrogen bond...
Autores principales: | , , , , , , |
---|---|
Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Nature Publishing Group UK
2017
|
Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5552783/ https://www.ncbi.nlm.nih.gov/pubmed/28798314 http://dx.doi.org/10.1038/s41467-017-00078-6 |
_version_ | 1783256517148934144 |
---|---|
author | Shi, Jiang-Ling Wang, Ding Zhang, Xi-Sha Li, Xiao-Lei Chen, Yu-Qin Li, Yu-Xue Shi, Zhang-Jie |
author_facet | Shi, Jiang-Ling Wang, Ding Zhang, Xi-Sha Li, Xiao-Lei Chen, Yu-Qin Li, Yu-Xue Shi, Zhang-Jie |
author_sort | Shi, Jiang-Ling |
collection | PubMed |
description | Metal-catalyzed cross-couplings provide powerful, concise, and accurate methods to construct carbon–carbon bonds from organohalides and organometallic reagents. Recent developments extended cross-couplings to reactions where one of the two partners connects with an aryl or alkyl carbon–hydrogen bond. From an economic and environmental point of view, oxidative couplings between two carbon–hydrogen bonds would be ideal. Oxidative coupling between phenyl and “inert” alkyl carbon–hydrogen bonds still awaits realization. It is very difficult to develop successful strategies for oxidative coupling of two carbon–hydrogen bonds owning different chemical properties. This article provides a solution to this challenge in a convenient preparation of dihydrobenzofurans from substituted phenyl alkyl ethers. For the phenyl carbon–hydrogen bond activation, our choice falls on the carboxylic acid fragment to form the palladacycle as a key intermediate. Through careful manipulation of an additional ligand, the second “inert” alkyl carbon–hydrogen bond activation takes place to facilitate the formation of structurally diversified dihydrobenzofurans. |
format | Online Article Text |
id | pubmed-5552783 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2017 |
publisher | Nature Publishing Group UK |
record_format | MEDLINE/PubMed |
spelling | pubmed-55527832017-08-15 Oxidative coupling of sp(2) and sp(3) carbon–hydrogen bonds to construct dihydrobenzofurans Shi, Jiang-Ling Wang, Ding Zhang, Xi-Sha Li, Xiao-Lei Chen, Yu-Qin Li, Yu-Xue Shi, Zhang-Jie Nat Commun Article Metal-catalyzed cross-couplings provide powerful, concise, and accurate methods to construct carbon–carbon bonds from organohalides and organometallic reagents. Recent developments extended cross-couplings to reactions where one of the two partners connects with an aryl or alkyl carbon–hydrogen bond. From an economic and environmental point of view, oxidative couplings between two carbon–hydrogen bonds would be ideal. Oxidative coupling between phenyl and “inert” alkyl carbon–hydrogen bonds still awaits realization. It is very difficult to develop successful strategies for oxidative coupling of two carbon–hydrogen bonds owning different chemical properties. This article provides a solution to this challenge in a convenient preparation of dihydrobenzofurans from substituted phenyl alkyl ethers. For the phenyl carbon–hydrogen bond activation, our choice falls on the carboxylic acid fragment to form the palladacycle as a key intermediate. Through careful manipulation of an additional ligand, the second “inert” alkyl carbon–hydrogen bond activation takes place to facilitate the formation of structurally diversified dihydrobenzofurans. Nature Publishing Group UK 2017-08-10 /pmc/articles/PMC5552783/ /pubmed/28798314 http://dx.doi.org/10.1038/s41467-017-00078-6 Text en © The Author(s) 2017 Open Access This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in a credit line to the material. If material is not included in the article’s Creative Commons license and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/. |
spellingShingle | Article Shi, Jiang-Ling Wang, Ding Zhang, Xi-Sha Li, Xiao-Lei Chen, Yu-Qin Li, Yu-Xue Shi, Zhang-Jie Oxidative coupling of sp(2) and sp(3) carbon–hydrogen bonds to construct dihydrobenzofurans |
title | Oxidative coupling of sp(2) and sp(3) carbon–hydrogen bonds to construct dihydrobenzofurans |
title_full | Oxidative coupling of sp(2) and sp(3) carbon–hydrogen bonds to construct dihydrobenzofurans |
title_fullStr | Oxidative coupling of sp(2) and sp(3) carbon–hydrogen bonds to construct dihydrobenzofurans |
title_full_unstemmed | Oxidative coupling of sp(2) and sp(3) carbon–hydrogen bonds to construct dihydrobenzofurans |
title_short | Oxidative coupling of sp(2) and sp(3) carbon–hydrogen bonds to construct dihydrobenzofurans |
title_sort | oxidative coupling of sp(2) and sp(3) carbon–hydrogen bonds to construct dihydrobenzofurans |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5552783/ https://www.ncbi.nlm.nih.gov/pubmed/28798314 http://dx.doi.org/10.1038/s41467-017-00078-6 |
work_keys_str_mv | AT shijiangling oxidativecouplingofsp2andsp3carbonhydrogenbondstoconstructdihydrobenzofurans AT wangding oxidativecouplingofsp2andsp3carbonhydrogenbondstoconstructdihydrobenzofurans AT zhangxisha oxidativecouplingofsp2andsp3carbonhydrogenbondstoconstructdihydrobenzofurans AT lixiaolei oxidativecouplingofsp2andsp3carbonhydrogenbondstoconstructdihydrobenzofurans AT chenyuqin oxidativecouplingofsp2andsp3carbonhydrogenbondstoconstructdihydrobenzofurans AT liyuxue oxidativecouplingofsp2andsp3carbonhydrogenbondstoconstructdihydrobenzofurans AT shizhangjie oxidativecouplingofsp2andsp3carbonhydrogenbondstoconstructdihydrobenzofurans |