Download Haloalkyne Chemistry by Huanfeng Jiang, Chuanle Zhu, Wanqing Wu PDF

By Huanfeng Jiang, Chuanle Zhu, Wanqing Wu

This publication provides effective and useful tools for the synthesis of assorted functionalized natural molecules from haloalkynes via diverse response techniques corresponding to cross-coupling reactions, nucleophilic additions and cycloadditions. It contains 4 chapters demonstrating fascinating examples of those ameliorations, and showcasing the unreal strength of haloalkynes for quick meeting of complicated molecular constructions. lots of the protocols let a number of bond-forming occasions to ensue in one operation, supplying possibilities to improve chemical synthesis and deal with the expanding calls for for eco-friendly and sustainable chemistry. It additionally provides a variety of functionalized items, together with many synthetically priceless conjugated cyclic and acyclic constructions that experience capability functions in fabrics technology, chemical biology and traditional product synthesis. This booklet is a worthwhile reference not just for natural chemists, but in addition for biologists and fabrics scientists inquisitive about the fashionable synthesis of natural compounds and fabrics.

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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) [143]. 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 [144]. 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.

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