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Copper-Catalyzed Aerobic Oxygenation of Benzylpyridine N-Oxides and Subsequent Post-Functionalization.
- Source :
-
Advanced Synthesis & Catalysis . Sep2017, Vol. 359 Issue 18, p3226-3236. 11p. - Publication Year :
- 2017
-
Abstract
- A copper-catalyzed aerobic oxidation of benzylpyridine N-oxides is reported. The N-oxide moiety acts as a built-in activator for the benzylic methylene oxidation, without requirement of additives. Reaction conditions were identified which suppress undesired benzoylpyridine formation via N-deoxygenation involving intermolecular oxygen transfer. The versatility of the N-oxide group of the benzoylpyridine N-oxide reaction products for post-functionalization of the pyridine ring is demonstrated through efficient C-C, C-N, C-O and C-Cl bond forming procedures, with both nucleophiles and electrophiles. Finally, the applicability of the new synthetic methodology is demonstrated in an alternative route towards the antihistaminic drug Acrivastine via three consecutive N-oxide activated C-H functionalization processes, starting from picoline N-oxide. [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 16154150
- Volume :
- 359
- Issue :
- 18
- Database :
- Academic Search Index
- Journal :
- Advanced Synthesis & Catalysis
- Publication Type :
- Academic Journal
- Accession number :
- 125201883
- Full Text :
- https://doi.org/10.1002/adsc.201700588