Abstract
Enhancing the sp³-hybridized character of molecular scaffolds (the "Escape from Flatland" strategy) is a crucial target to in-crease the probability of finding new drugs or agrochemicals. In this regard, an ideal platform is provided by three-component alkene difunctionalization reactions, which enable the simultaneous introduction of two distinct, orthogonal functional groups into the C=C bond in a single step. Herein, we report a photoredox catalyzed Ritter-type carboamidation of electronically di-verse styrenes harnessing non-stabilized, nucleophilic primary radicals generated from readily-accessible carboxylic acid-derived redox active esters. Furthermore, it was found that Heck-type products were chemoselectively obtained by simply switching aryl olefin acceptors with 1,1-diarylolefins. In the context of photocatalytic chemodivergence, various trisubstituted alkenes were synthesized. Both Ritter-Type and Heck-type olefin carbofunctionalizations were scalable up to 4 mmol scale in batch and continuous flow.
| Original language | English |
|---|---|
| Number of pages | 10 |
| DOIs | |
| Publication status | Published - 16 Jan 2025 |
Funding
M. L. and J. P. B. are members of the Elite Network of Bavaria Doctoral College: “IDK Chemical Catalysis with Photonic or Electric Energy Input” and M. L. is grateful to the ENB for financial support. I. D. is grateful for funding provided by the University of Regensburg and the SynCat programme of the ENB. C. P. and J. P. B. acknowledge funding formerly provided by the Alexander von Humboldt Foundation within the framework of the Sofja Kovalevskaja Award endowed to J. P. B. by the German Federal Ministry of Education and Research. J. P. B. is currently employed by the University of Strathclyde and is grateful for financial support.
Keywords
- Ritter amidation
- Heck reaction
- alkene difunctionalization
- chemodivergence
- photoredox catalysis
- multicomponent reaction
- radical polar crossover
- continuous flow