A facile one -pot synthesis of dihydroisobenzofuran derivatives by Passerini-azide/Ag(I)-catalyzed cyclization sequence has been developed. The Passerini-azide reactions of 2-(alkynyl)benzaldehydes, trimethylsilyl azide, and isocyanides gave tetrazole intermediates, which were transformed to the dihydroisobenzofurans in moderate to good yields via Ag(I)-catalyzed 5- exo - dig cyclization reaction.