Related Experiment Video
Updated: Apr 22, 2026

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
Higher-Order [10 + 2] Annulation Strategy for the Synthesis of CF3-Functionalized Benzopentalenes
Jaggaraju Prudhviraj1,2, Chavakula Nagababu1,2, Jagadeesh Babu Nanubolu2,3
1Fluoro-Agro Chemicals Division, CSIR-Indian Institute of Chemical Technology (CSIR-IICT), Hyderabad 500007, India.
Abstract:
Herein, we report a higher-order [10 + 2] annulation between indene-2-carbaldehydes and CF3-π-allyl-Pd complexes, enabling concise access to CF3-functionalized benzopentalenes. The reaction proceeds via an in situ generated isobenzofulvene intermediate and follows an unprecedented annulation that extends beyond the conventional reactivity of π-allyl-Pd species, delivering products with excellent diastereoselectivity. This work constitutes the first example of a higher-order annulation involving CF3-π-allyl-Pd species and expands the synthetic utility of indene-derived polyenolates in fluorinated polycycle synthesis.
More Related Videos
Related Concept Videos
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene
Nucleophilic Aromatic Substitution: Elimination–Addition
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions
Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene
Electrophilic Aromatic Substitution: Sulfonation of Benzene
Electrophilic Aromatic Substitution: Friedel–Crafts Acylation of Benzene

