Recent advances in the applications of gem-difluoromethylene alkynes
Chengmei Lu1, Yu Song1, Liuzhou Gao1
1School of Chemistry and Chemical Engineering, Yangzhou University, 180 Siwangting Road, Yangzhou, Jiangsu, 225002, P.R. China. wangyd021@yzu.edu.cn.
Abstract:
As a special class of alkynes, gem-difluoromethylene alkynes exhibit a variety of fascinating properties due to the presence of the gem-difluoro substitution. This substitution highlights the distinctive fluorine effects in influencing the chemoselectivity of reactions. As a result, chemical scientists have shown great interest and enthusiasm for investigating their reactions. In this review, we briefly summarize recent advances in transition metal-catalysed reactions of gem-difluoromethylene alkynes with multiple reaction pathways. Their mechanistic studies and challenges will be highlighted. The purpose of this review is to provide illustrations of elegant gem-difluoromethylene alkynes and thereby elicit further interest among synthetic chemists in developing innovative transformations of gem-difluoromethylene alkynes.
More Related Videos
08:43Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
09:54Chemoselective Preparation of 1-Iodoalkynes, 1,2-Diiodoalkenes, and 1,1,2-Triiodoalkenes Based on the Oxidative Iodination of Terminal Alkynes
Published on: September 12, 2018
Related Concept Videos
Preparation 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.
Electrophilic 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.
Electrophilic Addition to Alkynes: Hydrohalogenation
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene
Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)
Similar to cross-metathesis, ADMET also involves the formation of metallacyclobutane intermediate by [2+2] cycloaddition of one of the double bonds of a terminal diene with...
Preparation of Alkynes: Alkylation Reaction
Alkylation of terminal alkynes with primary alkyl halides in the presence of a strong base like sodium amide is one of the common methods for the synthesis of longer carbon-chain alkynes. For example, treatment of 1-propyne with sodium amide followed by reaction with ethyl bromide yields 2-pentyne.
