Lei, Tao and Appleson, Theresa and Breder, Alexander (2024) Intermolecular Aza-Wacker Coupling of Alkenes with Azoles by Photo-Aerobic Selenium-π-Acid Multicatalysis. ACS CATALYSIS, 14 (12). pp. 9586-9593. ISSN 2155-5435,
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Herein, the intermolecular, photoaerobic aza-Wacker coupling of azoles with alkenes by means of dual and ternary selenium-pi-acid multicatalysis is presented. The title method permits an expedited avenue toward a broad scope of N-allylated azoles and representative azinones under mild conditions with broad functional group tolerance, as is showcased in more than 60 examples including late-stage drug derivatizations. From a regiochemical perspective, the protocol is complementary to cognate photoredox catalytic olefin aminations, as they typically proceed through either allylic hydrogen atom abstraction or single electron oxidation of the alkene substrate. These methods predominantly result in C-N bond formations at the allylic periphery of the alkene or the less substituted position of the former pi-bond (i.e., anti-Markovnikov selectivity). The current process, however, operates through a radical-polar crossover mechanism, which solely affects the selenium catalyst, thus allowing the alkene to be converted strictly through an ionic two-electron transfer regime under Markovnikov control. In addition, it is shown that the corresponding N-vinyl azoles can also be accessed by sequential or one-pot treatment of the allylic azoles with base, thus emphasizing the exquisite utility of this method.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | ORGANOSELENIUM-CATALYZED SYNTHESIS; SYN-DICHLORINATION; AMINATION; FUNCTIONALIZATION; HETEROCYCLES; IMIDAZOLES; ALCOHOLS; INDOLES; OLEFINS; aza-Wacker coupling; azoles; alkenes; selenium-pi-acid catalysis; photoredox catalysis |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Organische Chemie Chemistry and Pharmacy > Institut für Organische Chemie > Arbeitskreis Prof. Dr. Alexander Breder |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 25 Jul 2025 08:05 |
| Last Modified: | 25 Jul 2025 08:05 |
| URI: | https://pred.uni-regensburg.de/id/eprint/63749 |
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