Journal
ORGANIC CHEMISTRY FRONTIERS
Volume 5, Issue 22, Pages -Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c8qo00988k
Keywords
-
Categories
Funding
- National Research Foundation of Korea (NRF) - Korean government (MSIP) [2016R1A4A1011189, 2017R1A2B2004786]
- Institute for Basic Science [IBS-R010-G1]
Ask authors/readers for more resources
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.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available