Construction of N-Ferrocene Substituted Benzodihydrooxazoles via a Catalyst-Free Aza-Michael Addition/C(sp(3))-O Bond Formation Tandem Reaction

A catalyst-free aza-Michael addition/C(sp(3))-O bond formation tandem reaction of substituted amino ferrocenes with quinone esters was developed, which provided a green and efficient strategy for the construction of a C(sp(3))-O bond from C(sp(3))-H, and a series of N-ferrocene-substituted benzodihy...

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Autores principales: Zhang, Mingliang, Zhao, Pin, Liu, Qilv, Liu, Xinlei, Hu, Jingya, Wu, Dongqing, Liu, Lantao
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2023
Materias:
Communication
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10384804/
https://www.ncbi.nlm.nih.gov/pubmed/37513488
http://dx.doi.org/10.3390/molecules28145615
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author Zhang, Mingliang
Zhao, Pin
Liu, Qilv
Liu, Xinlei
Hu, Jingya
Wu, Dongqing
Liu, Lantao
author_facet Zhang, Mingliang
Zhao, Pin
Liu, Qilv
Liu, Xinlei
Hu, Jingya
Wu, Dongqing
Liu, Lantao
author_sort Zhang, Mingliang
collection PubMed
description A catalyst-free aza-Michael addition/C(sp(3))-O bond formation tandem reaction of substituted amino ferrocenes with quinone esters was developed, which provided a green and efficient strategy for the construction of a C(sp(3))-O bond from C(sp(3))-H, and a series of N-ferrocene-substituted benzodihydrooxazoles were smoothly produced in moderate to excellent yields (up to >99% yield). The mechanism experiments showed that quinone esters performed as both substrate and oxidant. The salient features of this transformation include good functional group tolerance, broad substrate scope and mild conditions.
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spelling pubmed-103848042023-07-30 Construction of N-Ferrocene Substituted Benzodihydrooxazoles via a Catalyst-Free Aza-Michael Addition/C(sp(3))-O Bond Formation Tandem Reaction Zhang, Mingliang Zhao, Pin Liu, Qilv Liu, Xinlei Hu, Jingya Wu, Dongqing Liu, Lantao Molecules Communication A catalyst-free aza-Michael addition/C(sp(3))-O bond formation tandem reaction of substituted amino ferrocenes with quinone esters was developed, which provided a green and efficient strategy for the construction of a C(sp(3))-O bond from C(sp(3))-H, and a series of N-ferrocene-substituted benzodihydrooxazoles were smoothly produced in moderate to excellent yields (up to >99% yield). The mechanism experiments showed that quinone esters performed as both substrate and oxidant. The salient features of this transformation include good functional group tolerance, broad substrate scope and mild conditions. MDPI 2023-07-24 /pmc/articles/PMC10384804/ /pubmed/37513488 http://dx.doi.org/10.3390/molecules28145615 Text en © 2023 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Communication
Zhang, Mingliang
Zhao, Pin
Liu, Qilv
Liu, Xinlei
Hu, Jingya
Wu, Dongqing
Liu, Lantao
Construction of N-Ferrocene Substituted Benzodihydrooxazoles via a Catalyst-Free Aza-Michael Addition/C(sp(3))-O Bond Formation Tandem Reaction
title Construction of N-Ferrocene Substituted Benzodihydrooxazoles via a Catalyst-Free Aza-Michael Addition/C(sp(3))-O Bond Formation Tandem Reaction
title_full Construction of N-Ferrocene Substituted Benzodihydrooxazoles via a Catalyst-Free Aza-Michael Addition/C(sp(3))-O Bond Formation Tandem Reaction
title_fullStr Construction of N-Ferrocene Substituted Benzodihydrooxazoles via a Catalyst-Free Aza-Michael Addition/C(sp(3))-O Bond Formation Tandem Reaction
title_full_unstemmed Construction of N-Ferrocene Substituted Benzodihydrooxazoles via a Catalyst-Free Aza-Michael Addition/C(sp(3))-O Bond Formation Tandem Reaction
title_short Construction of N-Ferrocene Substituted Benzodihydrooxazoles via a Catalyst-Free Aza-Michael Addition/C(sp(3))-O Bond Formation Tandem Reaction
title_sort construction of n-ferrocene substituted benzodihydrooxazoles via a catalyst-free aza-michael addition/c(sp(3))-o bond formation tandem reaction
topic Communication
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10384804/
https://www.ncbi.nlm.nih.gov/pubmed/37513488
http://dx.doi.org/10.3390/molecules28145615
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