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

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Title
One-pot synthesis of 2-naphthols from nitrones and MBH adducts via decarboxylative N-O bond cleavage
Author(s)
Sang Hoon Han; Ashok Kumar Pandey; Heeyoung Lee; Saegun Kim; Dahye Kang; Young Hoon Jung; Hyung Sik Kim; Sungwoo Hong; In Su Kim
Publication Date
2018-11
Journal
ORGANIC CHEMISTRY FRONTIERS, v.5, no.22, pp.3210 - 3218
Publisher
ROYAL SOC CHEMISTRY
Abstract
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. ⓒthe Partner Organisations
URI
https://pr.ibs.re.kr/handle/8788114/5055
ISSN
2052-4129
Appears in Collections:
Center for Catalytic Hydrocarbon Functionalizations(분자활성 촉매반응 연구단) > Journal Papers (저널논문)
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