Cargando…

Ligand and counteranion enabled regiodivergent C–H bond functionalization of naphthols with α-aryl-α-diazoesters

Here, an unprecedented ligand and counteranion-controlled and site-selectivity switchable direct C–H bond functionalization of unprotected naphthols with α-aryl-α-diazoesters was developed. In this transformation, site selectivities are realized by turning on/off the coordination between metal compl...

Descripción completa

Detalles Bibliográficos
Autores principales: Yu, Zhunzhun, Li, Yongfeng, Zhang, Peichao, Liu, Lu, Zhang, Junliang
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2019
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6615435/
https://www.ncbi.nlm.nih.gov/pubmed/31367307
http://dx.doi.org/10.1039/c9sc01657k
_version_ 1783433366683516928
author Yu, Zhunzhun
Li, Yongfeng
Zhang, Peichao
Liu, Lu
Zhang, Junliang
author_facet Yu, Zhunzhun
Li, Yongfeng
Zhang, Peichao
Liu, Lu
Zhang, Junliang
author_sort Yu, Zhunzhun
collection PubMed
description Here, an unprecedented ligand and counteranion-controlled and site-selectivity switchable direct C–H bond functionalization of unprotected naphthols with α-aryl-α-diazoesters was developed. In this transformation, site selectivities are realized by turning on/off the coordination between metal complexes and hydroxy groups. The preliminary mechanism revealed that the interaction between the hydroxy group and gold catalyst plays a key role in switching the site-selectivity of gold-carbene. This protocol potentially provides a novel design for C–H bond functionalization.
format Online
Article
Text
id pubmed-6615435
institution National Center for Biotechnology Information
language English
publishDate 2019
publisher Royal Society of Chemistry
record_format MEDLINE/PubMed
spelling pubmed-66154352019-07-31 Ligand and counteranion enabled regiodivergent C–H bond functionalization of naphthols with α-aryl-α-diazoesters Yu, Zhunzhun Li, Yongfeng Zhang, Peichao Liu, Lu Zhang, Junliang Chem Sci Chemistry Here, an unprecedented ligand and counteranion-controlled and site-selectivity switchable direct C–H bond functionalization of unprotected naphthols with α-aryl-α-diazoesters was developed. In this transformation, site selectivities are realized by turning on/off the coordination between metal complexes and hydroxy groups. The preliminary mechanism revealed that the interaction between the hydroxy group and gold catalyst plays a key role in switching the site-selectivity of gold-carbene. This protocol potentially provides a novel design for C–H bond functionalization. Royal Society of Chemistry 2019-05-27 /pmc/articles/PMC6615435/ /pubmed/31367307 http://dx.doi.org/10.1039/c9sc01657k Text en This journal is © The Royal Society of Chemistry 2019 http://creativecommons.org/licenses/by-nc/3.0/ This article is freely available. This article is licensed under a Creative Commons Attribution Non Commercial 3.0 Unported Licence (CC BY-NC 3.0)
spellingShingle Chemistry
Yu, Zhunzhun
Li, Yongfeng
Zhang, Peichao
Liu, Lu
Zhang, Junliang
Ligand and counteranion enabled regiodivergent C–H bond functionalization of naphthols with α-aryl-α-diazoesters
title Ligand and counteranion enabled regiodivergent C–H bond functionalization of naphthols with α-aryl-α-diazoesters
title_full Ligand and counteranion enabled regiodivergent C–H bond functionalization of naphthols with α-aryl-α-diazoesters
title_fullStr Ligand and counteranion enabled regiodivergent C–H bond functionalization of naphthols with α-aryl-α-diazoesters
title_full_unstemmed Ligand and counteranion enabled regiodivergent C–H bond functionalization of naphthols with α-aryl-α-diazoesters
title_short Ligand and counteranion enabled regiodivergent C–H bond functionalization of naphthols with α-aryl-α-diazoesters
title_sort ligand and counteranion enabled regiodivergent c–h bond functionalization of naphthols with α-aryl-α-diazoesters
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6615435/
https://www.ncbi.nlm.nih.gov/pubmed/31367307
http://dx.doi.org/10.1039/c9sc01657k
work_keys_str_mv AT yuzhunzhun ligandandcounteranionenabledregiodivergentchbondfunctionalizationofnaphtholswithaaryladiazoesters
AT liyongfeng ligandandcounteranionenabledregiodivergentchbondfunctionalizationofnaphtholswithaaryladiazoesters
AT zhangpeichao ligandandcounteranionenabledregiodivergentchbondfunctionalizationofnaphtholswithaaryladiazoesters
AT liulu ligandandcounteranionenabledregiodivergentchbondfunctionalizationofnaphtholswithaaryladiazoesters
AT zhangjunliang ligandandcounteranionenabledregiodivergentchbondfunctionalizationofnaphtholswithaaryladiazoesters