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Copper-Catalyzed Sonogashira-Type Cross-Coupling of Trifluoroalkyl Bromides with Alkynes
Jian-Liang Yu1, Ya-Wen Zuo1, Yi-Gang Yang1
1Department of Chemistry, University of Science and Technology of China, 96 Jinzhai Road, Hefei, Anhui 230026, China.
Abstract:
Given the significance of propargyl trifluoromethyl scaffolds in drug discovery, the development of efficient synthetic approaches for their construction remains a pressing challenge. In this work, we present copper-catalyzed Sonogashira-type cross-coupling between trifluoroalkyl bromides and alkynes. This reaction proceeds under mild conditions with excellent regioselectivity, exhibits broad functional group tolerance across both aryl- and alkyl-substituted derivatives, and provides a practical and efficient approach for the synthesis of CF3-incorporated alkynes.
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One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
02:35Electrophilic Addition to Alkynes: Hydrohalogenation
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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.
02:24Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation
Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.
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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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Consider the bromination of cyclopentene. Molecular bromine is polarized in the proximity of the π electrons of cyclopentene. An electrophilic bromine atom adds across the double bond, forming a cyclic bromonium ion intermediate.