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Updated: Jan 3, 2026
A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
Transformation of Alkynes into α- or β-Difluorinated Alkyl Azides by an Efficient One-Pot Two-Step Procedure
Huaizhi Li1,2, Bhoomireddy Rajendra Prasad Reddy1, Xihe Bi1,2
1Jilin Province Key Laboratory of Organic Functional Molecular Design & Synthesis, Department of Chemistry , Northeast Normal University , Changchun 130024 , China.
Abstract:
Reported herein an unprecedented 1,2-azide migratory hydroazidation and subsequent gem-difluorination of alkynes accessing β-difluorinated alkyl azides. Importantly, functional group controlled 1,2-azide or 1,2-aryl migration was observed in the case of aromatic alkynes. Moreover, the azide group is sustained up to the final product. The method can be easily adapted for large-scale preparation, and the resulting products can be readily transformed into gem-difluoro group containing amine and triazole derivatives.
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02:34Preparation of Alkynes: Dehydrohalogenation
Alkynes can be prepared by dehydrohalogenation of vicinal or geminal dihalides in the presence of a strong base like sodium amide in liquid ammonia. The reaction proceeds with the loss of two equivalents of hydrogen halide (HX) via two successive E2 elimination reactions.
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02:38Electrophilic Addition to Alkynes: Halogenation
Halogenation is another class of electrophilic addition reactions where a halogen molecule gets added across a π bond. In alkynes, the presence of two π bonds allows for the addition of two equivalents of halogens (bromine or chlorine). The addition of the first halogen molecule forms a trans-dihaloalkene as the major product and the cis isomer as the minor product. Subsequent addition of the second equivalent yields the tetrahalide.
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