α‐Amidoaldehydes as Substrates in Rhodium‐Catalyzed Intermolecular Alkyne Hydroacylation: The Synthesis of α‐Amidoketones

We show that readily available α‐amidoaldehydes are effective substrates for intermolecular Rh‐catalyzed alkyne hydroacylation reactions. The catalyst [Rh(dppe)(C(6)H(5)F)][BAr(F) (4)] provides good reactivity, and allows a broad range of aldehydes and alkynes to be used as substrates, delivering α‐...

Descripción completa

Detalles Bibliográficos
Autores principales: Pal, Ritashree, O'Brien, Sean C., Willis, Michael C.
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/PMC7540332/
https://www.ncbi.nlm.nih.gov/pubmed/32449532
http://dx.doi.org/10.1002/chem.202002478
_version_ 1783591183777267712
author Pal, Ritashree
O'Brien, Sean C.
Willis, Michael C.
author_facet Pal, Ritashree
O'Brien, Sean C.
Willis, Michael C.
author_sort Pal, Ritashree
collection PubMed
description We show that readily available α‐amidoaldehydes are effective substrates for intermolecular Rh‐catalyzed alkyne hydroacylation reactions. The catalyst [Rh(dppe)(C(6)H(5)F)][BAr(F) (4)] provides good reactivity, and allows a broad range of aldehydes and alkynes to be used as substrates, delivering α‐amidoketone products. High yields and high levels of regioselectivity are achieved. The use of α‐amidoaldehydes as substrates establishes that 1,4‐dicarbonyl motifs can be used as controlling groups in Rh‐catalyzed hydroacylation reactions.
format Online
Article
Text
id pubmed-7540332
institution National Center for Biotechnology Information
language English
publishDate 2020
publisher John Wiley and Sons Inc.
record_format MEDLINE/PubMed
spelling pubmed-75403322020-10-09 α‐Amidoaldehydes as Substrates in Rhodium‐Catalyzed Intermolecular Alkyne Hydroacylation: The Synthesis of α‐Amidoketones Pal, Ritashree O'Brien, Sean C. Willis, Michael C. Chemistry Communications We show that readily available α‐amidoaldehydes are effective substrates for intermolecular Rh‐catalyzed alkyne hydroacylation reactions. The catalyst [Rh(dppe)(C(6)H(5)F)][BAr(F) (4)] provides good reactivity, and allows a broad range of aldehydes and alkynes to be used as substrates, delivering α‐amidoketone products. High yields and high levels of regioselectivity are achieved. The use of α‐amidoaldehydes as substrates establishes that 1,4‐dicarbonyl motifs can be used as controlling groups in Rh‐catalyzed hydroacylation reactions. John Wiley and Sons Inc. 2020-07-30 2020-09-10 /pmc/articles/PMC7540332/ /pubmed/32449532 http://dx.doi.org/10.1002/chem.202002478 Text en © 2020 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA 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
Pal, Ritashree
O'Brien, Sean C.
Willis, Michael C.
α‐Amidoaldehydes as Substrates in Rhodium‐Catalyzed Intermolecular Alkyne Hydroacylation: The Synthesis of α‐Amidoketones
title α‐Amidoaldehydes as Substrates in Rhodium‐Catalyzed Intermolecular Alkyne Hydroacylation: The Synthesis of α‐Amidoketones
title_full α‐Amidoaldehydes as Substrates in Rhodium‐Catalyzed Intermolecular Alkyne Hydroacylation: The Synthesis of α‐Amidoketones
title_fullStr α‐Amidoaldehydes as Substrates in Rhodium‐Catalyzed Intermolecular Alkyne Hydroacylation: The Synthesis of α‐Amidoketones
title_full_unstemmed α‐Amidoaldehydes as Substrates in Rhodium‐Catalyzed Intermolecular Alkyne Hydroacylation: The Synthesis of α‐Amidoketones
title_short α‐Amidoaldehydes as Substrates in Rhodium‐Catalyzed Intermolecular Alkyne Hydroacylation: The Synthesis of α‐Amidoketones
title_sort α‐amidoaldehydes as substrates in rhodium‐catalyzed intermolecular alkyne hydroacylation: the synthesis of α‐amidoketones
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7540332/
https://www.ncbi.nlm.nih.gov/pubmed/32449532
http://dx.doi.org/10.1002/chem.202002478
work_keys_str_mv AT palritashree aamidoaldehydesassubstratesinrhodiumcatalyzedintermolecularalkynehydroacylationthesynthesisofaamidoketones
AT obrienseanc aamidoaldehydesassubstratesinrhodiumcatalyzedintermolecularalkynehydroacylationthesynthesisofaamidoketones
AT willismichaelc aamidoaldehydesassubstratesinrhodiumcatalyzedintermolecularalkynehydroacylationthesynthesisofaamidoketones

Ejemplares similares