Rhodium(III)-Catalyzed C-H Bond Activation and [3+3] Spirocyclization of Benzoxazines with CF3-Imidoyl Sulfoxonium
Qihua Chen1, Zhenye Cui1, Zhengkai Chen1
1School of Chemistry and Chemical Engineering, Zhejiang Sci-Tech University, Hangzhou 310018, China.
Abstract:
Rh(III)-catalyzed C-H bond activation and spirocyclization of benzoxazines with CF3-imidoyl sulfoxonium ylides (TFISYs) have been achieved, providing a direct and facile avenue to structurally diverse trifluoromethyl-substituted spiroheterocycles. The transformation involves a cascade C-H activation, tautomerization, and intramolecular nucleophilic addition pathway. A broad spectrum of spiroheterocycle molecules containing biologically important benzoxazine and isoquinoline skeletons are synthesized in up to 98% yields.
Related Concept Videos
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene
Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions
Preparation and Reactions of Sulfides
ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3
Reactions at the Benzylic Position: Halogenation

![Solid-phase Synthesis of [4.4] Spirocyclic Oximes](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F58508.jpg&w=3840&q=50)
