Unkel, Lisa-Natascha and Malcherek, Simon and Schendera, Eva and Hoffmann, Frank and Rehbein, Julia and Brasholz, Malte (2019) Photoorganocatalytic Aerobic Oxidative Amine Dehydrogenation/Super Acid-Mediated Pictet-Spengler Cyclization: Synthesis of cis-1,3-Diaryl Tetrahydroisoquinolines. ADVANCED SYNTHESIS & CATALYSIS, 361 (12). pp. 2870-2876. ISSN 1615-4150, 1615-4169
Full text not available from this repository. (Request a copy)Abstract
Aerobic oxidative dehydrogenation reactions of benzylamines to imines were studied and the efficiencies of various ground- and excited state quinone organocatalysts were compared. Long wave-absorbing anthraquinones readily catalyze the aerobic photodehydrogenation of primary and secondary benzylamines to benzylidenebenzylamines with high rate and selectivity, and the reaction mechanism was studied by laser flash photolysis. Further, branched alpha-benzyl dibenzyl-amines undergo a regioselective photocatalytic dehydrogenation to branched aldimines, which can efficiently be converted into cis-1,3-diaryl tetrahydro-isoquinolines through diastereoselective super acid-mediated Pictet-Spengler cyclizations.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | ASYMMETRIC HYDROGENATION; PHOTOREDOX CATALYSIS; ISOQUINOLINIUM SALTS; SECONDARY; EFFICIENT; ORGANOCATALYSIS; PHOTOCATALYSIS; ANTHRAQUINONES; BENZYLAMINES; DERIVATIVES; photocatalysis; aerobic oxidation; imines; heterocycles; super acids |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Organische Chemie |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 06 Apr 2020 08:14 |
| Last Modified: | 27 Apr 2020 05:11 |
| URI: | https://pred.uni-regensburg.de/id/eprint/26821 |
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