Photocatalytic Reactions of α-CF3 Alkenes with Alcohols by Controllable Non-, Mono- and Dual-Defluorination
Meixue Gan1, Shuyue Zhang1, Wenting Ye1
1Guangxi Key Laboratory of Clean Pulp & Papermaking and Pollution Control, School of Light Industrial and Food Engineering, Guangxi University, Nanning 530004, China.
None:
Herein, we present a chemoselective strategy for the divergent synthesis of γ-trifluoromethyl alcohols and difluorohomoallyl alcohols via photoredox-catalyzed hydroxyalkylation of α-CF3 alkenes with primary/secondary alcohols. Both products can further undergo base-mediated intramolecular defluorinative cyclization to construct monofluorinated dihydrofurans in a one-pot process. Through controllable C-F bond cleavage, this approach enables streamlined synthesis of three types of fluorinated products from abundant and inexpensive raw materials under mild photoredox conditions.
Related Concept Videos
Acid-Catalyzed α-Halogenation of Aldehydes and Ketones
In the first step of the mechanism, the acid protonates the carbonyl oxygen resulting in a resonance-stabilized cation, which subsequently loses an α-hydrogen to form an enol tautomer. The C=C bond in an enol is highly nucleophilic because of the electron-donating nature of the –OH group. Consequently, the double bond attacks an electrophilic halogen to form a...
Acid-Catalyzed Dehydration of Alcohols to Alkenes
Base-Promoted α-Halogenation of Aldehydes and Ketones
Hydroboration-Oxidation of Alkenes
Preparation of Alcohols via Addition Reactions
The acid-catalyzed addition of water to the double bond of alkenes is a large-scale industrial method used to synthesize low-molecular-weight alcohols. An acidic atmosphere is required to allow the hydrogen in the water molecule to act as an electrophile and attack the double bond in an alkene. The addition of a proton to the double bond creates a carbocation intermediate. The proton preferentially bonds to the less substituted end of the double bond to create a more stable carbocation...
Reactions of Aldehydes and Ketones: Baeyer–Villiger Oxidation
The carbonyl center is...


