Rhodium(II)‐Catalyzed Site‐Selective Intramolecular Insertion of Aryldiazoacetates into Unactivated Primary C−H Bond: A Direct Route to 2‐Unsubstituted Indanes. Issue 14 (15th June 2022)

• Record Type: Journal Article
• Authors: Nambu, Hisanori; Amano, Ryoya; Tamura, Takafumi; Yakura, Takayuki
• Is Part Of: Advanced synthesis & catalysis. Volume 364:Issue 14(2022)
• Page Start: 2422
• Page End: 2428
• Publication Date: 2022-06-15
• Subjects: C−H insertion -- carbenoids -- carbocycles -- primary C−H bond -- rhodium; Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.202200115
• Languages: English
• ISSNs: 1615-4150

Abstract

Abstract: Dirhodium(II)‐catalyzed intramolecular insertion of aryldiazoacetates into an unactivated primary C−H bond was described in this study. The insertion reaction of aryldiazoacetates with ortho ‐isopropyl or ortho ‐ethyl groups in the presence of a catalytic amount of dirhodium(II) tetrakis(triphenylacetate), Rh2 (tpa)4, at room temperature proceeded site‐selectively to afford 2‐unsubstituted indane‐1‐carboxylates in 75%–96% yields. In the case of o ‐isopropyl‐substituted aryldiazoacetates, cis ‐isomers were obtained as major products. Furthermore, a chemoselective C−H insertion reaction of aryldiazoacetate bearing 1‐oxyethyl‐substituent at the ortho position was achieved by using a bulky and electron‐deficient pivaloyl group as the protecting group of a highly active oxygen atom. The present reaction provided a direct route to 2‐unsubstituted indanes. Abstract :