Designer HF-Based Fluorination Reagent: Highly Regioselective Synthesis of Fluoroalkenes and gem-Difluoromethylene Compounds from Alkynes | Zendy

Otome E. Okoromoba | Zendy; Junbin Han | Zendy; Gerald B. Hammond | Zendy; Bo Xu | Zendy

Open Access

Designer HF-Based Fluorination Reagent: Highly Regioselective Synthesis of Fluoroalkenes and gem-Difluoromethylene Compounds from Alkynes

Author(s) -

Otome E. Okoromoba,

Junbin Han,

Gerald B. Hammond,

Bo Xu

Publication year - 2014

Publication title -

journal of the american chemical society

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 7.115

H-Index - 612

eISSN - 1520-5126

pISSN - 0002-7863

DOI - 10.1021/ja508369z

Subject(s) - chemistry , regioselectivity , reagent , cationic polymerization , nucleophile , catalysis , hydrogen bond , combinatorial chemistry , organic chemistry , hydrogen fluoride , medicinal chemistry , molecule

Hydrogen fluoride (HF) and selected nonbasic and weakly coordinating (toward cationic metal) hydrogen-bond acceptors (e.g., DMPU) can form stable complexes through hydrogen bonding. The DMPU/HF complex is a new nucleophilic fluorination reagent that has high acidity and is compatible with cationic metal catalysts. The gold-catalyzed mono- and dihydrofluorination of alkynes using the DMPU/HF complex yields synthetically important fluoroalkenes and gem-difluoromethlylene compounds regioselectively.

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