10-Hydroxy-10,9-boroxarophenanthrenes: Versatile synthetic intermediates to 3,4-benzocoumarins and triaryls

Q. Jean Zhou, Karin Worm, Roland E. Dolle

Research output: Contribution to journalArticlepeer-review

105 Scopus citations

Abstract

10-Hydroxy-10,9-boroxarophenanthrenes were obtained as unexpected major products upon BBr3-mediated O-demethylation of 2-methoxybiaryls. The formation likely proceeds via intramolecular electrophilic aromatic cyclization of a reactive dibromoaryloxyborane intermediate. Essentially quantitative yields of 10-hydroxy-10,9-boroxarophenanthrenes were also obtained from 2-hydroxybiaryl and BCl3/AlCl3 with use of a modified literature procedure. As synthetic intermediates, 10-hydroxy-10,9- boroxarophenanthrenes were efficiently converted to 3,4-benzocoumarins and triaryls through Pd-catalyzed CO insertion and Suzuki reaction.

Original languageEnglish
Pages (from-to)5147-5149
Number of pages3
JournalJournal of Organic Chemistry
Volume69
Issue number15
DOIs
StatePublished - Jul 23 2004

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