Spirocyclic Oxindole and Dihydrobenzofuran Formation via a Dearomative Cyclization–Nucleophilic Trapping Sequence
Abstract
Dearomative difunctionalization of heteroarenes represents a convenient method toward heteroalicyclic compounds by breaking the aromaticity and forming two chemical bonds in a single step. Herein, a palladium-catalyzed alkenyletherification of indoles is disclosed through dearomative spirocyclization of C 3-alkyne-tethered indoles, followed by intermolecular nucleophilic addition of the generated iminium with MeOH, affording a series of spirooxindoles in moderate to good yields after an additional oxidation. In addition, dearomative alkenylacetoxylation of C 3-alkyne-tethered benzofurans with AcOH is also achieved toward spirodihydrobenzofurans in moderate to excellent yields. Preliminary exploration of the asymmetric version and synthetic transformation of the product are investigated.
Fields of Study & Subjects
Catalytic C–H Functionalization Methods
Catalytic Alkyne Reactions
Catalytic Cross-Coupling Reactions
Publication details
- Journal / source
- The Journal of Organic Chemistry
- Publisher
- American Chemical Society (ACS)
- Volume
- 91
- Issue
- 2
- Pages
- 1004–1016
- Publication date
- 7 January 2026
- Language
- EN