Murugesan, Kathiravan and Donabauer, Karsten and Narobe, Rok and Derdau, Volker and Bauer, Armin and Koenig, Burkhard (2022) Photoredox-Catalyzed Site-Selective Generation of Carbanions from C(sp3 )-H Bonds in Amines. ACS CATALYSIS, 12 (7). pp. 3974-3984. ISSN 2155-5435,
Full text not available from this repository. (Request a copy)Abstract
The selective activation of sp3 carbon-hydrogen bonds in the presence of multiple C-H bonds is challenging and remains of supreme importance in chemical research. Late-stage modification of complex molecules via sp3 C-H activation is of high prevalence in organic synthesis. Herein, we describe the activation of a C(sp3 )-H bond in the alpha-position to an amine via a carbanion intermediate. In the presence of several alpha-amine sites, only one specific position is selectively activated. Applying this protocol, the proposed carbanion intermediate was effectively trapped with different electrophiles such as deuterium (D+ ), tritium (T+ ), or carbonyl compounds compiling over 50 examples. Further, this methodology was used to install deuterium or tritium in different drug-derivatives (>10 drugs) at a selected position in a late-stage functionalization. In addition, the protocol is suitable for a gram-scale synthesis, and a detailed mechanistic investigation has been carried out to support our hypothesis.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | C-H; C(SP(3))-H BONDS; ATOM TRANSFER; FUNCTIONALIZATION; DEUTERATION; ALDEHYDES; EQUIVALENTS; ALLYLATION; TRITIATION; ALCOHOLS; photoredox catalysis; carbanion; site-selectivity; isotope labeling; amino alcohols; C-H functionalization |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Burkhard König |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 01 Feb 2024 11:19 |
| Last Modified: | 01 Feb 2024 11:19 |
| URI: | https://pred.uni-regensburg.de/id/eprint/57203 |
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