Highly efficient synthesis of 9-aminoxanthenes via the tandem reaction of arynes with salicyl N-tosylimines

o-Silylaryl Triflates: A Journey of Kobayashi Aryne Precursors

“…440 N-tosylimines could also serve as electrophiles in this type of transformations. In this context, the groups of He 441 and Lu 442 independently reported an efficient preparation of 9-aminoxanthenes 6-10 from salicyl N-tosylimines 6-9 and arynes (Scheme 74d). Recently, Yoshida et al disclosed that the reaction between S-(2hydroxyaryl) 4-toluenethiosulfonates 6-11 (X = O) and osilylaryl triflates could furnish phenoxathiins 6-12 (X = O) (Scheme 74e).…”

Multicomponent Reaction of Phosphines, Benzynes, and CO2: Facile Synthesis of Stable Zwitterionic Phosphonium Inner Salts

“…However, these zwitterions are unstable and have not been successfully prepared. With our continuing interest in benzyne chemistry, we found that phosphines, benzynes, and CO 2 can undergo a three-component coupling reaction to produce zwitterionic species as the unexpected final products . These stable zwitterions, also named phosphonium salts, are a unique type of P­(V) compounds that are used widely as organocatalysts, organic reagents, ionic liquids, ligands, and others in organic chemistry.…”

Direct Assembly of Polysubstituted Naphthalenes via a Tandem Reaction of Benzynes and α-Cyano-β-methylenones

“…In line with our continued interest in benzyne chemistry, we hypothesized that α-cyano-β-methylenones, which have been used successfully by Ye, − Wang, and Shi as C4 synthon partners in the synthesis of polysubstituted benzenes, may undergo benzannulation with benzynes to form polysubstituted naphthalenes (Scheme e). Herein, we report our development on the construction of polysubstituted naphthalenes.…”