Soft Propargylic Deprotonation: Designed Ligand Enables Au-Catalyzed Isomerization of Alkynes to 1,3-Dienes

[Image: see text] By functionalizing the privileged biphenyl-2-ylphosphine with a basic amino group at the rarely explored 3′ position, the derived gold(I) complex possesses orthogonally positioned “push” and “pull” forces, which enable for the first time soft propargylic deprotonation and permit th...

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Autores principales: Wang, Zhixun, Wang, Yanzhao, Zhang, Liming
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2014
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4089065/
https://www.ncbi.nlm.nih.gov/pubmed/24911158
http://dx.doi.org/10.1021/ja503909c
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author Wang, Zhixun
Wang, Yanzhao
Zhang, Liming
author_facet Wang, Zhixun
Wang, Yanzhao
Zhang, Liming
author_sort Wang, Zhixun
collection PubMed
description [Image: see text] By functionalizing the privileged biphenyl-2-ylphosphine with a basic amino group at the rarely explored 3′ position, the derived gold(I) complex possesses orthogonally positioned “push” and “pull” forces, which enable for the first time soft propargylic deprotonation and permit the bridging of a difference of >26 pK(a) units (in DMSO) between a propargylic hydrogen and a protonated tertiary aniline. The application of this design led to efficient isomerization of alkynes into versatile 1,3-dienes with synthetically useful scope under mild reaction conditions.
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spelling pubmed-40890652015-06-09 Soft Propargylic Deprotonation: Designed Ligand Enables Au-Catalyzed Isomerization of Alkynes to 1,3-Dienes Wang, Zhixun Wang, Yanzhao Zhang, Liming J Am Chem Soc [Image: see text] By functionalizing the privileged biphenyl-2-ylphosphine with a basic amino group at the rarely explored 3′ position, the derived gold(I) complex possesses orthogonally positioned “push” and “pull” forces, which enable for the first time soft propargylic deprotonation and permit the bridging of a difference of >26 pK(a) units (in DMSO) between a propargylic hydrogen and a protonated tertiary aniline. The application of this design led to efficient isomerization of alkynes into versatile 1,3-dienes with synthetically useful scope under mild reaction conditions. American Chemical Society 2014-06-09 2014-06-25 /pmc/articles/PMC4089065/ /pubmed/24911158 http://dx.doi.org/10.1021/ja503909c Text en Copyright © 2014 American Chemical Society Open Access on 06/09/2015
spellingShingle Wang, Zhixun
Wang, Yanzhao
Zhang, Liming
Soft Propargylic Deprotonation: Designed Ligand Enables Au-Catalyzed Isomerization of Alkynes to 1,3-Dienes
title Soft Propargylic Deprotonation: Designed Ligand Enables Au-Catalyzed Isomerization of Alkynes to 1,3-Dienes
title_full Soft Propargylic Deprotonation: Designed Ligand Enables Au-Catalyzed Isomerization of Alkynes to 1,3-Dienes
title_fullStr Soft Propargylic Deprotonation: Designed Ligand Enables Au-Catalyzed Isomerization of Alkynes to 1,3-Dienes
title_full_unstemmed Soft Propargylic Deprotonation: Designed Ligand Enables Au-Catalyzed Isomerization of Alkynes to 1,3-Dienes
title_short Soft Propargylic Deprotonation: Designed Ligand Enables Au-Catalyzed Isomerization of Alkynes to 1,3-Dienes
title_sort soft propargylic deprotonation: designed ligand enables au-catalyzed isomerization of alkynes to 1,3-dienes
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4089065/
https://www.ncbi.nlm.nih.gov/pubmed/24911158
http://dx.doi.org/10.1021/ja503909c
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AT wangyanzhao softpropargylicdeprotonationdesignedligandenablesaucatalyzedisomerizationofalkynesto13dienes
AT zhangliming softpropargylicdeprotonationdesignedligandenablesaucatalyzedisomerizationofalkynesto13dienes

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