Benzyne with epoxides

S. Beltran-Rodil, D. Pena, E. Guitian, Reaction of benzyne with styrene oxide insertion of arynes into a C-O bond of epoxides, Synlett 8 (2007) 1308-1310. 

The decarboxylation of diazotized anthranilic acid carried out by Stiles and Miller49 is also a fragmentation reaction it affords dehydrobenzene (benzyne), which reacts at once as a dienophile with, e.g., furan, giving 1-naphthol by way of an epoxide. 

The generated phosphide boranes are extremely nucleophilic and reacted smoothly with activated alkyl halides (entries 3-7), epoxides (entries 1, 2 and 8) and molecules with activated multiple bonds such as ethyl acrylate (entry 9), benzyne (10) or even fullerene (entry 14). Some C2-symmetric diphosphine... 

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