Cargando…

Decarbonylative Borylation of Amides by Palladium Catalysis

[Image: see text] The development of transition-metal-catalyzed borylation reactions is of significant importance for the fields of organic synthesis and medicinal chemistry because of the versatility of organoboron functional groups. Herein, we report the direct decarbonylative borylation of amides...

Descripción completa

Detalles Bibliográficos
Autores principales: Shi, Shicheng, Szostak, Michal
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2019
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6647946/
https://www.ncbi.nlm.nih.gov/pubmed/31459674
http://dx.doi.org/10.1021/acsomega.9b00081
_version_ 1783437777505878016
author Shi, Shicheng
Szostak, Michal
author_facet Shi, Shicheng
Szostak, Michal
author_sort Shi, Shicheng
collection PubMed
description [Image: see text] The development of transition-metal-catalyzed borylation reactions is of significant importance for the fields of organic synthesis and medicinal chemistry because of the versatility of organoboron functional groups. Herein, we report the direct decarbonylative borylation of amides by highly selective carbon–nitrogen bond cleavage by palladium catalysis. The approach capitalizes on the ground-state destabilization of the amide bond in N-acyl glutarimides to achieve Pd-catalyzed insertion into the amide N–C bond and decarbonylation (deamidation). Mechanistic studies and the utility of this methodology in orthogonal sequential cross-couplings of robust, bench-stable amides are reported.
format Online
Article
Text
id pubmed-6647946
institution National Center for Biotechnology Information
language English
publishDate 2019
publisher American Chemical Society
record_format MEDLINE/PubMed
spelling pubmed-66479462019-08-27 Decarbonylative Borylation of Amides by Palladium Catalysis Shi, Shicheng Szostak, Michal ACS Omega [Image: see text] The development of transition-metal-catalyzed borylation reactions is of significant importance for the fields of organic synthesis and medicinal chemistry because of the versatility of organoboron functional groups. Herein, we report the direct decarbonylative borylation of amides by highly selective carbon–nitrogen bond cleavage by palladium catalysis. The approach capitalizes on the ground-state destabilization of the amide bond in N-acyl glutarimides to achieve Pd-catalyzed insertion into the amide N–C bond and decarbonylation (deamidation). Mechanistic studies and the utility of this methodology in orthogonal sequential cross-couplings of robust, bench-stable amides are reported. American Chemical Society 2019-03-05 /pmc/articles/PMC6647946/ /pubmed/31459674 http://dx.doi.org/10.1021/acsomega.9b00081 Text en Copyright © 2019 American Chemical Society This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes.
spellingShingle Shi, Shicheng
Szostak, Michal
Decarbonylative Borylation of Amides by Palladium Catalysis
title Decarbonylative Borylation of Amides by Palladium Catalysis
title_full Decarbonylative Borylation of Amides by Palladium Catalysis
title_fullStr Decarbonylative Borylation of Amides by Palladium Catalysis
title_full_unstemmed Decarbonylative Borylation of Amides by Palladium Catalysis
title_short Decarbonylative Borylation of Amides by Palladium Catalysis
title_sort decarbonylative borylation of amides by palladium catalysis
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6647946/
https://www.ncbi.nlm.nih.gov/pubmed/31459674
http://dx.doi.org/10.1021/acsomega.9b00081
work_keys_str_mv AT shishicheng decarbonylativeborylationofamidesbypalladiumcatalysis
AT szostakmichal decarbonylativeborylationofamidesbypalladiumcatalysis