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Updated: Jan 1, 2026

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
Published on: May 26, 2019
Three-component vicinal-diarylation of alkenes via direct transmetalation of arylboronic acids
Yun Zhang1, Gong Chen1, Dongbing Zhao1
1State Key Laboratory and Institute of Elemento-Organic Chemistry , College of Chemistry , Nankai University , 94 Weijin Road , Tianjin 300071 , China . Email: gongchen@nankai.edu.cn ;
Abstract:
Herein, we report three-component vicinal-diarylation of non-conjugated alkenes initiated by transmetalation of arylboronic acids, which provides complementary access to β,γ-diaryl carbonyl compounds. We have also screened a large number of chiral ligands for developing an enantioselective version of this reaction and obtained the preliminary results (up to 79 : 21 e.r.). Notably, the methodology developed herein represents the first three component syn-vicinal-dicarbofunctionalization of non-conjugated alkenes involving palladium catalysis.
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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.
Hydroboration-Oxidation of Alkenes
Reduction 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.
Halogenation of Alkenes
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.

