Functionalization of α‐C(sp(3))−H Bonds in Amides Using Radical Translocating Arylating Groups

α‐C−H arylation of N‐alkylamides using 2‐iodoarylsulfonyl radical translocating arylating (RTA) groups is reported. The method allows the construction of α‐quaternary carbon centers in amides. Various mono‐ and disubstituted RTA‐groups are applied to the arylation of primary, secondary, and tertiary...

Descripción completa

Detalles Bibliográficos
Autores principales: Radhoff, Niklas, Studer, Armido
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2020
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7898318/
https://www.ncbi.nlm.nih.gov/pubmed/33215815
http://dx.doi.org/10.1002/anie.202013275
_version_ 1783653838673149952
author Radhoff, Niklas
Studer, Armido
author_facet Radhoff, Niklas
Studer, Armido
author_sort Radhoff, Niklas
collection PubMed
description α‐C−H arylation of N‐alkylamides using 2‐iodoarylsulfonyl radical translocating arylating (RTA) groups is reported. The method allows the construction of α‐quaternary carbon centers in amides. Various mono‐ and disubstituted RTA‐groups are applied to the arylation of primary, secondary, and tertiary α‐C(sp(3))−H‐bonds. These radical transformations proceed in good to excellent yields and the cascades comprise a 1,6‐hydrogen atom transfer, followed by a 1,4‐aryl migration with subsequent SO(2) extrusion.
format Online
Article
Text
id pubmed-7898318
institution National Center for Biotechnology Information
language English
publishDate 2020
publisher John Wiley and Sons Inc.
record_format MEDLINE/PubMed
spelling pubmed-78983182021-03-03 Functionalization of α‐C(sp(3))−H Bonds in Amides Using Radical Translocating Arylating Groups Radhoff, Niklas Studer, Armido Angew Chem Int Ed Engl Communications α‐C−H arylation of N‐alkylamides using 2‐iodoarylsulfonyl radical translocating arylating (RTA) groups is reported. The method allows the construction of α‐quaternary carbon centers in amides. Various mono‐ and disubstituted RTA‐groups are applied to the arylation of primary, secondary, and tertiary α‐C(sp(3))−H‐bonds. These radical transformations proceed in good to excellent yields and the cascades comprise a 1,6‐hydrogen atom transfer, followed by a 1,4‐aryl migration with subsequent SO(2) extrusion. John Wiley and Sons Inc. 2020-12-30 2021-02-15 /pmc/articles/PMC7898318/ /pubmed/33215815 http://dx.doi.org/10.1002/anie.202013275 Text en © 2020 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH This is an open access article under the terms of the http://creativecommons.org/licenses/by/4.0/ License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
spellingShingle Communications
Radhoff, Niklas
Studer, Armido
Functionalization of α‐C(sp(3))−H Bonds in Amides Using Radical Translocating Arylating Groups
title Functionalization of α‐C(sp(3))−H Bonds in Amides Using Radical Translocating Arylating Groups
title_full Functionalization of α‐C(sp(3))−H Bonds in Amides Using Radical Translocating Arylating Groups
title_fullStr Functionalization of α‐C(sp(3))−H Bonds in Amides Using Radical Translocating Arylating Groups
title_full_unstemmed Functionalization of α‐C(sp(3))−H Bonds in Amides Using Radical Translocating Arylating Groups
title_short Functionalization of α‐C(sp(3))−H Bonds in Amides Using Radical Translocating Arylating Groups
title_sort functionalization of α‐c(sp(3))−h bonds in amides using radical translocating arylating groups
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7898318/
https://www.ncbi.nlm.nih.gov/pubmed/33215815
http://dx.doi.org/10.1002/anie.202013275
work_keys_str_mv AT radhoffniklas functionalizationofacsp3hbondsinamidesusingradicaltranslocatingarylatinggroups
AT studerarmido functionalizationofacsp3hbondsinamidesusingradicaltranslocatingarylatinggroups

Ejemplares similares