Tian, Xianhai and Kaur, Jaspreet and Yakubov, Shahboz and Barham, Joshua P. (2022) alpha-Amino Radical Halogen Atom Transfer Agents for Metallaphotoredox-Catalyzed Cross-Electrophile Couplings of Distinct Organic Halides. CHEMSUSCHEM, 15 (15): e202200906. ISSN 1864-5631, 1864-564X
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alpha-Amino radicals from simple tertiary amines were employed as halogen atom transfer (XAT) agents in metallaphotoredox catalysis for cross-electrophile couplings of organic bromides with organic iodides. This XAT strategy proved to be efficient for the generation of carbon radicals from a range of partners (alkyl, aryl, alkenyl, and alkynyl iodides). The reactivities of these radical intermediates were captured by nickel catalysis with organobromides including aryl, heteroaryl, alkenyl, and alkyl bromides, enabling six diverse C-C bond formations. Classic named reactions including Negishi, Suzuki, Heck, and Sonogashira reactions were readily achieved in a net-reductive fashion under mild conditions. More importantly, the cross coupling was viable with either organic bromide or iodide as limiting reactant based on the availability of substrates, which is beneficial to the late-stage functionalization of complex molecules. The scalability of this method in batch and flow was investigated, further demonstrating its applicability.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | ARYL BROMIDES; PHOTOREDOX CATALYSIS; UNACTIVATED ALKYL; ACTIVATION; LIGHT; TRIFLUOROMETHYLATION; UNLOCKING; FLUORINE; cross coupling; halogen atom transfer; late-stage functionalization; nickel catalysis; photocatalysis |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Organische Chemie |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 05 Dec 2023 09:33 |
| Last Modified: | 05 Dec 2023 09:33 |
| URI: | https://pred.uni-regensburg.de/id/eprint/56885 |
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