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Title
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Copper-catalyzed aerobic oxygenation of benzylpyridine N-oxides and subsequent post-functionalization
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Author
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Abstract
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| 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. |
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Language
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English
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Source (journal)
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Advanced synthesis and catalysis. - Weinheim, 2001, currens
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Publication
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Weinheim
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2017
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ISSN
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1615-4150
[print]
1615-4169
[online]
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DOI
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10.1002/ADSC.201700588
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Volume/pages
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359
:18
(2017)
, p. 3226-3236
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ISI
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000411034800019
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Full text (Publisher's DOI)
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Full text (open access)
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Full text (publisher's version - intranet only)
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