Rh()-Catalyzed C-H bond activation/annulation reactions of arylacyl ammonium salts with 4-diazoisochroman-3-imines and 4-diazoisoquinolin-3-ones

Herein, we report a C-H bond functionalization strategy for the construction of oxo- and aza-spirocyclic compounds from diazo compounds as coupling partners. Our method comprises ortho sp 2 C-H bond activation of arylacyl ammonium salts, followed by coupling with two types of cyclic diazo compounds i.e. 4-diazoisochroman-3-imines and 4-diazoisoquinolin-3-ones, respectively. The mechanism involves the formation of dual metal carbene intermediates in situ with the breakage of oxidizing C-N bonds in arylacyl ammonium salts. The cascade C-H activation/annulation process gave a variety of novel spiro[indene-1,4′-isochromane]-3,3′(2 H )-diones and spiro[indene-1,4′-isoquinoline]-3,3′(2 H )-diones in good to excellent yields. Readily available starting materials, broad substrate scope, and operationally simple and mild reaction conditions are the prominent features of this method. A convenient approach to novel oxo - and aza -spirocyclic compounds via a C-H bond functionalization of arylacyl ammonium salts with 4-diazoisochroman-3-imines and 4-diazoisoquinolin-3-ones is reported.