H2020Индивидуална стипендия2019–2021

BICACH · Novel bifunctional HAT catalysts for site-divergent C-H functionalizations mediated by photoredox catalysis

„Хоризонт 2020“ — Действия „Мария Склодовска-Кюри“

Период: 2019-05-01 → 2021-04-30
Финансиране от ЕС: 162 806 €
Участници: 1
Схема: MSCA-IF

Линиите свързват координатора с партньорите.

Накратко на български

Алканът, основен компонент на природния газ и петрола, се изследва като източник за създаване на сложни химикали чрез активиране на неговите въглеродно-водородни връзки с помощта на видима светлина. Това помага за намаляване на химическите отпадъци и синтеза на вещества с нови свойства.

Този кратък обзор е генериран от изкуствен интелект

Кратко обяснение, генерирано от езиков модел по текста на CORDIS. Оригиналът е по-долу.

Резултати накратко

Novel bifunctional HAT catalysts for site-divergent C-H functionalizations mediated by photoredox catalysis

Alkanes are the major components of natural gas and oil which are abundantly produced by the petrochemical industry. They are almost exclusively used as a source of energy following their combustion which can be considered as a waste of a carbon-based feedstock. From the organic chemist’s point of view, alkanes indeed represent a major carbon pool for chemical synthesis which remains poorly explored. To date, the elaboration of complex organic molecules heavily relies on the introduction and manipulation of functional groups, typically carbon-oxygen or carbon-halogen bonds. In this regard, the direct functionalization of aliphatic carbon-hydrogen (C-H) bonds, the most abundant moiety within alkanes, represents a more ideal approach to access molecular complexity. However, there are two major hurdles toward he application of this strategy. First, alkane C-H bonds are very difficult to activate. However, if one can overcome this lack of reactivity, it should then face a daunting selectivity issue: how to activate selectively one single C-H bond within an alkane backbone harnessing many almost identical C-H bonds? The development of chemical processes enabling the selective conversion of cheap and abundant alkanes into high-value chemicals is one of the Holy grail in organic synthesis. Such endeavour would strongly benefit our society 1) By reducing the amount of chemical waste to access valuable chemical products; 2) By enabling the synthesis of new chemicals with unprecedented properties. The main objective of this project was to develop a library of small molecules enabling the selective functionalization of alkane through catalytic processes using visible light as a renewable source of energy.

Текст от CORDIS, на английски · Данни: CORDIS, © Европейски съюз

Цел на проекта

The direct catalytic functionalization of C-H bonds, an ubiquitous motif in organic molecules, represents a paradigm shift in the standard logic of organic synthesis. One of the major challenges to render this approach synthetically useful is to control the site-selectivity because most organic molecules exhibit several similar aliphatic C-H bonds.The functionalization of aliphatic C-H bond mediated by photoredox catalysis is a highly active field of research. To date, state-of-the-art site-selective methods in this field rely on substrate control which are inherently restricted to the functionalization of a single C-H bond within the substrate backbone. The innovative aspect of this research program is to target catalyst control to allow the site-selective functionalization of several different C-H bonds of a single substrate. Through this approach, we wish to go beyond the challenging problem of site-selectivity to enable site-divergent functionalizations. Such a breakthrough would provide a new tool for a flexible and streamlined access to molecular complexity from chemical feedstocks.To achieve our objectives, we plan to develop novel bifunctional catalysts incorporating one moiety able to engage into dynamic non-covalent interactions with the substrate and another functional group able to perform Hydrogen Atom Transfer (HAT) processes. These two functional groups are connected by an inert spacer which will position the HAT unit in proximity to a particular C-H bond of the substrate, thus controlling site-selectivity for the C-H activation event. By varying the nature of the spacer, we expect to selectively functionalize several different positions of linear alkyl chains possessing almost undistinguishable methylene C-H bonds.Overall, BICACH aims at using simple bifunctional organocatalysts and light energy to trigger highly challenging C-H functionalization processes. In addition, it offers a unique training to the ER with broad future research perspectives.

Оригинален текст от CORDIS (на английски).

Участници

UNIVERSITAET REGENSBURG · RegensburgКоординаторГермания