NHC2Breslow · Mechanistic Studies of NHC Organocatalysis – Quantifying the Reactivity of the Breslow Intermediate
„Хоризонт 2020“ — Действия „Мария Склодовска-Кюри“
- Период
- 2022-03-01 → 2024-02-29
- Финансиране от ЕС
- 212 934 €
- Участници
- 1
- Схема
- MSCA-IF
Линиите свързват координатора с партньорите.
Накратко на български
Химичните реакции с органични катализатори се анализират чрез изследване на поведението на т.нар. междинно съединение на Бреслоу, например при взаимодействието му с различни михаелови акцептори. Това помага за създаването на устойчиви методи за синтез на нови органични материали.
Кратко обяснение, генерирано от езиков модел по текста на CORDIS. Оригиналът е по-долу.
Резултати накратко
Mechanistic Studies of NHC Organocatalysis – Quantifying the Reactivity of the Breslow Intermediate
The main aim of this proposal was to generate a quantitative understanding of the behaviour of the so called Breslow Intermediate that has been implicated in NHC based catalysis. This proposal aimed to deliver quantitative underpinning knowledge of this key intermediate that could (i) be used to develop a fundamental scale to quantify BI reactivity with a range of electrophilic species and (ii) be applied to answer unresolved mechanistic and chemoselectivity questions in contemporary NHC-based catalysis. Work in this project has achieved - for the first time - a novel kinetic approach othat allows the relative quantification and reactivity of diverse Michael acceptors when they interact with the presumed N-C6F5 Breslow intermediate in the intermolecular Stetter reaction. This encompasses all workpackages WP1-WP6 and goes beyond the current state-of-the-art. The new synthetic methods developed that use catalytic quantities of non-toxic organocatalysts to generate new chiral organic materials address issues relating to sustainability. Futhermore the mechanistic insight generated will be of widespread interest to the synthetic community and industry and so may longer term have significant benefits for society. Potential users of the project results are other academic groups around the world alongside industry who recognise the mechanistic insight provided.
Текст от CORDIS, на английски · Данни: CORDIS, © Европейски съюз
Цел на проекта
N-heterocyclic carbenes (NHCs) are the most versatile class of organocatalyst, allowing access to a variety of catalytic intermediates for the construction of complex targets from simple starting materials under mild conditions. Despite many individual conceptual advances in this field, it is not understood (or even commonly acknowledged by practitioners) why product distributions of NHC-catalysed processes often differ dramatically with catalyst scaffold or with subtle substituent variation within an NHC-catalyst family. Following the many synthetic innovations over the past decade, future transformative benefits will rely on the careful, quantitative and detailed analysis and understanding of all aspects of reactions mechanisms in order to make informed choice of catalyst for a given transformation, rather then relying on brute force screening. To break from this traditional, time-intensive screening approach and fully realize the potential of NHCs, a quantitative mechanistic understanding is required. Central to this state-of-the-art field is the catalytically competent “Breslow intermediate” (BI) that is regarded as the cornerstone of modern NHC-mediated catalysis. First characterised in 2012, its reactivity is key to a multitude of synthetic transformations. Despite its importance, a quantitative understanding of the behaviour of this transiently formed species has yet to be defined. This proposal will deliver quantitative underpinning knowledge of this key intermediate that will (i) be used to develop a fundamental scale to quantify BI reactivity with a range of electrophilic species and (ii) be applied to answer unresolved mechanistic and chemoselectivity questions in contemporary NHC-based catalysis.
Оригинален текст от CORDIS (на английски).
Участници
- THE UNIVERSITY COURT OF THE UNIVERSITY OF ST ANDREWS · ST ANDREWSКоординаторОбединеното кралство
Връзки
Данни: CORDIS, © Европейски съюз