Rh(iii)-Catalyzed C–H bond activation/annulation reactions of arylacyl ammonium salts with 4-diazoisochroman-3-imines and 4-diazoisoquinolin-3-ones. Issue 9 (15th February 2022)

• Record Type: Journal Article
• Authors: Suleman, Muhammad; Qi, Minghui; Xie, Jianwei; Lu, Ping; Wang, Yanguang
• Is Part Of: Organic & biomolecular chemistry. Volume 20:Issue 9(2022)
• Page Start: 1900
• Page End: 1906
• Publication Date: 2022-02-15
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/d1ob02405a
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : 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. Abstract : 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.