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Updated: Aug 8, 2026

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
Regio-Reversed α-Addition of Oxygen-Centered Nucleophiles to Carbazole-Based Trifluoromethyl Alkenes
Yuan-Yuan He1, Nian-Nian Li1, Lan Qin1
1Key Laboratory of Catalysis and Energy Materials Chemistry of Ministry of Education & Hubei Key Laboratory of Catalysis and Materials Science, School of Chemistry and Materials Science, South-Central Minzu University, Wuhan430074, China.
Abstract:
The conjugate addition of nucleophiles to electron-deficient alkenes represents one of the most powerful methods for forming chemical bonds. While this process typically demonstrates β-selectivity, the regio-reversed α-additions have largely been underexplored. In this study, we present an unprecedented α-specific nucleophilic addition of weak oxygen-centered nucleophiles to carbazole-based trifluoromethyl alkenes, achieved through a photoinduced polarity transduction pathway under mild, photocatalyst-free conditions. This reaction exhibits a broad scope, good functional group tolerance, exceptional α-regioselectivity and allows for late-stage skeletal diversification and polymer modification.
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