By Huanfeng Jiang, Chuanle Zhu, Wanqing Wu
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Additional resources for Haloalkyne Chemistry
They proposed that the haloalkyne intermediate was ﬁrst generated and then the triple bond attacked the Ag cation to deliver a π-complex 41, which was transferred to the corresponding σ-complex 42 through the nucleophilic attack of acetic anion. Finally, protonation of 42 gave the desired β-haloenol acetate product. Accordingly, the high regio- and stereoselectivities might be owing to the stabilization effect of halogen atom to the Ag catalyst. Later, plenty of methods have been developed for the nucleophilic addition of haloalkynes with diverse oxygen nucleophiles, and delivered the corresponding β-haloenol [184, 185] or αhaloketone [186, 187] derivatives in good yields.
34) . This method was transition-metal free, and exhibited excellent functional group compatibility. 2 Transformations of Carbon-Carbon Triple Bond Motif 39 asymmetrical (Z)-enediynes in good yields through selective Sonogashira coupling pathway. Later in 2012, Zhu and co-workers realized the hydrohalogenation of alkynyl halides to construct (Z)-1,2-dihaloalkenes under palladium catalysis . 5 mL) were heated at 120 °C for 6 h. Then, the mixture was allowed to cool to room temperature, and water was added.
13 GaCl3-catalyzed ortho-ethynylation of phenols Yamaguchi and co-workers reported GaCl3-catalyzed ortho-ethynylation of phenols. Various substituted phenols were applicable to this method, and the turnover number based on the catalyst (GaCl3) was between 8 and 10. The mechanism studies indicated this catalytic ethynylation involved carbogallation of haloalkyne and the formation of intermediate 10 under the effect of lithium salts. Interestingly, the protonated product of intermediate 11 was not detected in the reaction mixture.