An Unexpected Inactivation of N-Heterocyclic Carbene Organic Catalyst by 1-Methylcyclopropylcarbaldehyde and 2,2,2-Trifluoroacetophenone

An unprecedented inactivation process of the indanol-derived NHC catalysts bearing N-C(6)F(5) groups is reported. An unexpected multi-cyclic complex product is obtained from the 3-component reaction with the 1-methylcyclopropyl-carbaldehyde, the 2,2,2-trifluoroacetophenone and the NHC catalyst. The...

Descripción completa

Detalles Bibliográficos
Autores principales: Chen, Yanling, Lv, Jie, Pan, Xuling, Jin, Zhichao
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Frontiers Media S.A. 2022
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8988059/
https://www.ncbi.nlm.nih.gov/pubmed/35402372
http://dx.doi.org/10.3389/fchem.2022.875286
_version_ 1784682878929469440
author Chen, Yanling
Lv, Jie
Pan, Xuling
Jin, Zhichao
author_facet Chen, Yanling
Lv, Jie
Pan, Xuling
Jin, Zhichao
author_sort Chen, Yanling
collection PubMed
description An unprecedented inactivation process of the indanol-derived NHC catalysts bearing N-C(6)F(5) groups is reported. An unexpected multi-cyclic complex product is obtained from the 3-component reaction with the 1-methylcyclopropyl-carbaldehyde, the 2,2,2-trifluoroacetophenone and the NHC catalyst. The absolute structure of the inactivation product is unambiguously assigned via X-ray analysis on its single crystals. The formation of the structurally complex product is rationalized through a multi-step cascade cyclization process.
format Online
Article
Text
id pubmed-8988059
institution National Center for Biotechnology Information
language English
publishDate 2022
publisher Frontiers Media S.A.
record_format MEDLINE/PubMed
spelling pubmed-89880592022-04-08 An Unexpected Inactivation of N-Heterocyclic Carbene Organic Catalyst by 1-Methylcyclopropylcarbaldehyde and 2,2,2-Trifluoroacetophenone Chen, Yanling Lv, Jie Pan, Xuling Jin, Zhichao Front Chem Chemistry An unprecedented inactivation process of the indanol-derived NHC catalysts bearing N-C(6)F(5) groups is reported. An unexpected multi-cyclic complex product is obtained from the 3-component reaction with the 1-methylcyclopropyl-carbaldehyde, the 2,2,2-trifluoroacetophenone and the NHC catalyst. The absolute structure of the inactivation product is unambiguously assigned via X-ray analysis on its single crystals. The formation of the structurally complex product is rationalized through a multi-step cascade cyclization process. Frontiers Media S.A. 2022-03-24 /pmc/articles/PMC8988059/ /pubmed/35402372 http://dx.doi.org/10.3389/fchem.2022.875286 Text en Copyright © 2022 Chen, Lv, Pan and Jin. https://creativecommons.org/licenses/by/4.0/This is an open-access article distributed under the terms of the Creative Commons Attribution License (CC BY). The use, distribution or reproduction in other forums is permitted, provided the original author(s) and the copyright owner(s) are credited and that the original publication in this journal is cited, in accordance with accepted academic practice. No use, distribution or reproduction is permitted which does not comply with these terms.
spellingShingle Chemistry
Chen, Yanling
Lv, Jie
Pan, Xuling
Jin, Zhichao
An Unexpected Inactivation of N-Heterocyclic Carbene Organic Catalyst by 1-Methylcyclopropylcarbaldehyde and 2,2,2-Trifluoroacetophenone
title An Unexpected Inactivation of N-Heterocyclic Carbene Organic Catalyst by 1-Methylcyclopropylcarbaldehyde and 2,2,2-Trifluoroacetophenone
title_full An Unexpected Inactivation of N-Heterocyclic Carbene Organic Catalyst by 1-Methylcyclopropylcarbaldehyde and 2,2,2-Trifluoroacetophenone
title_fullStr An Unexpected Inactivation of N-Heterocyclic Carbene Organic Catalyst by 1-Methylcyclopropylcarbaldehyde and 2,2,2-Trifluoroacetophenone
title_full_unstemmed An Unexpected Inactivation of N-Heterocyclic Carbene Organic Catalyst by 1-Methylcyclopropylcarbaldehyde and 2,2,2-Trifluoroacetophenone
title_short An Unexpected Inactivation of N-Heterocyclic Carbene Organic Catalyst by 1-Methylcyclopropylcarbaldehyde and 2,2,2-Trifluoroacetophenone
title_sort unexpected inactivation of n-heterocyclic carbene organic catalyst by 1-methylcyclopropylcarbaldehyde and 2,2,2-trifluoroacetophenone
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8988059/
https://www.ncbi.nlm.nih.gov/pubmed/35402372
http://dx.doi.org/10.3389/fchem.2022.875286
work_keys_str_mv AT chenyanling anunexpectedinactivationofnheterocycliccarbeneorganiccatalystby1methylcyclopropylcarbaldehydeand222trifluoroacetophenone
AT lvjie anunexpectedinactivationofnheterocycliccarbeneorganiccatalystby1methylcyclopropylcarbaldehydeand222trifluoroacetophenone
AT panxuling anunexpectedinactivationofnheterocycliccarbeneorganiccatalystby1methylcyclopropylcarbaldehydeand222trifluoroacetophenone
AT jinzhichao anunexpectedinactivationofnheterocycliccarbeneorganiccatalystby1methylcyclopropylcarbaldehydeand222trifluoroacetophenone
AT chenyanling unexpectedinactivationofnheterocycliccarbeneorganiccatalystby1methylcyclopropylcarbaldehydeand222trifluoroacetophenone
AT lvjie unexpectedinactivationofnheterocycliccarbeneorganiccatalystby1methylcyclopropylcarbaldehydeand222trifluoroacetophenone
AT panxuling unexpectedinactivationofnheterocycliccarbeneorganiccatalystby1methylcyclopropylcarbaldehydeand222trifluoroacetophenone
AT jinzhichao unexpectedinactivationofnheterocycliccarbeneorganiccatalystby1methylcyclopropylcarbaldehydeand222trifluoroacetophenone

Ejemplares similares