Staudinger Cleavages of Amides on Naphthalene for the Ipsilateral Effect of 1,8-Substituents.

8-(Azidomethyl)-1-naphthoic acid was elaborately prepared, and its coupling with amines provided the corresponding 8-(azidomethyl)-1-naphthamides. The Staudinger reactions of 8-(azidomethyl)-1-naphthamides with phosphine produced iminophosphoranes, and easy intramolecular cyclization of the iminophosphoranes afforded 2,3-dihydro-1-benzo[]isoquinolin-1-one leaving amines with almost quantitative conversion rates for the ipsilateral effect of 1,8-substituents on naphthalene. The protocol exhibits some advantages, including a readily available protecting group, cleavages of amides in almost quantitative conversion rates, an aqueous medium, reactions at room temperature, a broad substrate scope, wide functional group tolerance, and suitable scale-up reactions.

Sodium trifluoromethanesulfinate-mediated photocatalytic aerobic oxidative esterification of aromatic aldehydes and alcohols.

A sodium trifluoromethanesulfinate-mediated photocatalytic strategy for the aerobic oxidative esterification of aromatic aldehydes and alcohols has been developed, in which the formed pentacoordinate sulfide derived from readily available and inexpensive sodium trifluoromethanesulfinate and oxygen acts as the photocatalyst, and the corresponding aromatic esters were provided in moderate to good yields. The present method is an economical and environmentally friendly protocol.