Stille vs. Suzuki – cross-coupling for the functionalization of diazocines

Diazocines are azobenzene derived macrocyclic photoswitches with well resolved photostationary states for the (E)- and (Z)-isomers, which improves their addressability by light. In this work, effective procedures for the stannylation and borylation of diazocines in different positions are reported....

Descripción completa

Detalles Bibliográficos
Autores principales: Walther, Melanie, Kipke, Waldemar, Renken, Raul, Staubitz, Anne
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2023
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10227463/
https://www.ncbi.nlm.nih.gov/pubmed/37260568
http://dx.doi.org/10.1039/d3ra02988c
_version_ 1785050778179731456
author Walther, Melanie
Kipke, Waldemar
Renken, Raul
Staubitz, Anne
author_facet Walther, Melanie
Kipke, Waldemar
Renken, Raul
Staubitz, Anne
author_sort Walther, Melanie
collection PubMed
description Diazocines are azobenzene derived macrocyclic photoswitches with well resolved photostationary states for the (E)- and (Z)-isomers, which improves their addressability by light. In this work, effective procedures for the stannylation and borylation of diazocines in different positions are reported. Their use in Stille cross-coupling and Suzuki cross-coupling reactions with organic bromides is demonstrated in yields of 47–94% (Stille cross-coupling) and 0–95% (Suzuki cross-coupling), respectively.
format Online
Article
Text
id pubmed-10227463
institution National Center for Biotechnology Information
language English
publishDate 2023
publisher The Royal Society of Chemistry
record_format MEDLINE/PubMed
spelling pubmed-102274632023-05-31 Stille vs. Suzuki – cross-coupling for the functionalization of diazocines Walther, Melanie Kipke, Waldemar Renken, Raul Staubitz, Anne RSC Adv Chemistry Diazocines are azobenzene derived macrocyclic photoswitches with well resolved photostationary states for the (E)- and (Z)-isomers, which improves their addressability by light. In this work, effective procedures for the stannylation and borylation of diazocines in different positions are reported. Their use in Stille cross-coupling and Suzuki cross-coupling reactions with organic bromides is demonstrated in yields of 47–94% (Stille cross-coupling) and 0–95% (Suzuki cross-coupling), respectively. The Royal Society of Chemistry 2023-05-30 /pmc/articles/PMC10227463/ /pubmed/37260568 http://dx.doi.org/10.1039/d3ra02988c Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Walther, Melanie
Kipke, Waldemar
Renken, Raul
Staubitz, Anne
Stille vs. Suzuki – cross-coupling for the functionalization of diazocines
title Stille vs. Suzuki – cross-coupling for the functionalization of diazocines
title_full Stille vs. Suzuki – cross-coupling for the functionalization of diazocines
title_fullStr Stille vs. Suzuki – cross-coupling for the functionalization of diazocines
title_full_unstemmed Stille vs. Suzuki – cross-coupling for the functionalization of diazocines
title_short Stille vs. Suzuki – cross-coupling for the functionalization of diazocines
title_sort stille vs. suzuki – cross-coupling for the functionalization of diazocines
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10227463/
https://www.ncbi.nlm.nih.gov/pubmed/37260568
http://dx.doi.org/10.1039/d3ra02988c
work_keys_str_mv AT walthermelanie stillevssuzukicrosscouplingforthefunctionalizationofdiazocines
AT kipkewaldemar stillevssuzukicrosscouplingforthefunctionalizationofdiazocines
AT renkenraul stillevssuzukicrosscouplingforthefunctionalizationofdiazocines
AT staubitzanne stillevssuzukicrosscouplingforthefunctionalizationofdiazocines

Ejemplares similares