Integrative Theory/Experiment-Driven Exploration of a Multicomponent Reaction towards Imidazoline-2-(thi)ones

Art Kruithof; Jos R. Mulder; J. M. Ruiz; Elwin Janssen; M. Mooijman; Eelco Ruijter; Celia Fonseca Guerra; F. Matthias Bickelhaupt; Romano V. A. Orru

doi:10.1002/ejoc.201700941

Integrative Theory/Experiment-Driven Exploration of a Multicomponent Reaction towards Imidazoline-2-(thi)ones

Art Kruithof, Jos R. Mulder, J. M. Ruiz, Elwin Janssen, M. Mooijman, Eelco Ruijter, Celia Fonseca Guerra, F. Matthias Bickelhaupt^*, Romano V. A. Orru

^*Corresponding author for this work

Research output: Contribution to Journal › Article › Academic › peer-review

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Abstract

Predicting reactivity in multicomponent reactions (MCRs) is extremely difficult. These reactions proceed by multiple pathways and are inherently associated with a potentially large variation of reactants and functional groups. To date, theoretical chemistry has been used in hindsight to verify experimental observations. However, its use in the early stages of the development of a (multicomponent) reaction process can prevent laborious and time-consuming optimization studies by pinpointing the most relevant parameter(s) in the reactivity, thus focusing experimental efforts. Herein, we discuss a study that truly integrates theoretical and synthetic chemistry to unravel in full detail the complex and intricate reaction characteristics of the novel versatile MCR of α-acidic iso(thio)cyanates, amines and aldehydes to access densely functionalized imidazoline-2-(thi)ones.

Original language	English
Pages (from-to)	104-112
Number of pages	9
Journal	European Journal of Organic Chemistry
Volume	2018
Issue number	1
DOIs	https://doi.org/10.1002/ejoc.201700941
Publication status	Published - 10 Jan 2018

Funding

F. J. J. de Kanter and A. W. Ehlers are kindly acknowledged for maintaining the NMR facilities. The Ministerio de Ciencia e Inno-vacion (MICINN), the Fundacion Española para la Ciencia y la Tecnologıa (FECYT), the National Research School of Combination – Catalysis (NRSC-C), the Netherlands Organization for Scientific Research (NWO-CW, NWO-NCF, NWO-EW) and the Dutch Astrochemistry Network (DAN) supported by NWO are all acknowledged for funding.

Funders	Funder number
Dutch Astrochemistry Network
Ministerio de Ciencia e Inno-vacion
NWO-CW
NWO-EW
NWO-NCF
National Research School of Combination – Catalysis
Nederlandse Organisatie voor Wetenschappelijk Onderzoek
Fundación Española para la Ciencia y la Tecnología

Keywords

Computer chemistry
Density functional calculations
Multicomponent reactions
Nitrogen heterocycles
Synthesis design

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10.1002/ejoc.201700941

Kruithof_et_al-2018-European_Journal_of_Organic_ChemistryFinal published version, 1.46 MBLicence: Article 25fa Dutch Copyright Act

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abstract = "Predicting reactivity in multicomponent reactions (MCRs) is extremely difficult. These reactions proceed by multiple pathways and are inherently associated with a potentially large variation of reactants and functional groups. To date, theoretical chemistry has been used in hindsight to verify experimental observations. However, its use in the early stages of the development of a (multicomponent) reaction process can prevent laborious and time-consuming optimization studies by pinpointing the most relevant parameter(s) in the reactivity, thus focusing experimental efforts. Herein, we discuss a study that truly integrates theoretical and synthetic chemistry to unravel in full detail the complex and intricate reaction characteristics of the novel versatile MCR of α-acidic iso(thio)cyanates, amines and aldehydes to access densely functionalized imidazoline-2-(thi)ones.",

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AU - Janssen, Elwin

AU - Mooijman, M.

AU - Ruijter, Eelco

AU - Guerra, Celia Fonseca

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AU - Orru, Romano V. A.

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AB - Predicting reactivity in multicomponent reactions (MCRs) is extremely difficult. These reactions proceed by multiple pathways and are inherently associated with a potentially large variation of reactants and functional groups. To date, theoretical chemistry has been used in hindsight to verify experimental observations. However, its use in the early stages of the development of a (multicomponent) reaction process can prevent laborious and time-consuming optimization studies by pinpointing the most relevant parameter(s) in the reactivity, thus focusing experimental efforts. Herein, we discuss a study that truly integrates theoretical and synthetic chemistry to unravel in full detail the complex and intricate reaction characteristics of the novel versatile MCR of α-acidic iso(thio)cyanates, amines and aldehydes to access densely functionalized imidazoline-2-(thi)ones.

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Integrative Theory/Experiment-Driven Exploration of a Multicomponent Reaction towards Imidazoline-2-(thi)ones

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