One-pot synthesis of 2-naphthols from nitrones and MBH adducts via decarboxylative N-O bond cleavage

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The efficient synthesis of 2-naphthols is important for their further development as bioactive compounds and chiral ligands as well as other synthetic purposes. Herein, we describe the unprecedented one-pot synthesis of 2-naphthols through an acid-mediated decarboxylative N-O bond cleavage of bridged benzoxazepine intermediates, which were in turn generated from aryl nitrones and Morita-Baylis-Hillman (MBH) adducts under cationic rhodium(iii) catalysis. A range of 2-naphthol derivatives including anthracen-2-ol, phenanthren-2-ol, and 11H-benzo[b]fluoren-7-ol were formed with excellent site selectivities and functional group compatibilities. To gain mechanistic insight into this process, a series of mechanistic investigations and DFT calculations were also performed.
Publisher
ROYAL SOC CHEMISTRY
Issue Date
2018-11
Language
English
Article Type
Article
Keywords

C-H ACTIVATION; BETA-HYDROXY KETONES; ADDITION-DIECKMANN CONDENSATION; CATALYZED HYDROXYLATION; ASYMMETRIC CATALYSIS; ARYL HALIDES; MILD; NEOCARZINOSTATIN; CYCLOADDITION; NAPHTHALENES

Citation

ORGANIC CHEMISTRY FRONTIERS, v.5, no.22

ISSN
2052-4129
DOI
10.1039/c8qo00988k
URI
http://hdl.handle.net/10203/247124
Appears in Collection
CH-Journal Papers(저널논문)
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