Haloalkyne Chemistry by Huanfeng Jiang, Chuanle Zhu, Wanqing Wu

By Huanfeng Jiang, Chuanle Zhu, Wanqing Wu

This ebook provides effective and functional equipment for the synthesis of varied functionalized natural molecules from haloalkynes via diversified response strategies akin to cross-coupling reactions, nucleophilic additions and cycloadditions. It includes 4 chapters demonstrating attention-grabbing examples of those modifications, and showcasing the bogus energy 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, providing possibilities to boost 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 helpful conjugated cyclic and acyclic constructions that experience capability functions in fabrics technological know-how, chemical biology and average product synthesis. This ebook is a beneficial reference not just for natural chemists, but additionally for biologists and fabrics scientists considering the fashionable synthesis of natural compounds and fabrics.

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Haloalkyne Chemistry

This booklet offers effective and useful equipment for the synthesis of assorted functionalized natural molecules from haloalkynes via various response approaches corresponding to cross-coupling reactions, nucleophilic additions and cycloadditions. It includes 4 chapters demonstrating fascinating examples of those changes, and showcasing the artificial energy of haloalkynes for quick meeting of advanced molecular constructions.

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The resulting mixture was extracted with ethyl acetate (15 mL × 3), and the combined extract was dried with anhydrous MgSO4. The solvent was removed under reduced pressure and the residue was separated by column chromatography to give the desired dihaloalkenes. Due to the unique physical and biological properties of fluorinated molecules, the corresponding vinyl fluoride products were quite attractive for synthetic and medicinal chemists [145–149]. Although the halide nucleoaddition to haloalkynes have provided a diverse set of haloalkene derivatives, the incorporation of fluorine atom into the final olefin products through transition metal catalysis is still a challenging target.

42). Later, Jiang’s group [172] documented the nucleophilic addition of isocyanides to bromoalkynes via palladium catalysis, and Vadola [173] realized the gold-catalyzed dearomative spirocyclization of aryl alkynoate esters. General Procedure Indium-Catalyzed Addition of 1,3-Dicarbonyl Compounds to 1-Iodoalkynes: A mixture of 1,3-dicarbonyl compound (2 mmol), 1-iodoalkyne (3 mmol), and In(NTf2)3 (5 mol%) in toluene (2 mL) was heated in the dark at 70 °C for 4 h. The mixture was filtered through a pad of silica gel and concentrated.

As an additional benefit, the 5-iodo-1,2,3-triazole adducts are versatile synthetic intermediates, which are amenable to further functionalization. Later, GarcíaÁlvarez [202], Rowan [203], Zhu [204], and Díez-González [205] independently reported the cycloaddition of azides with haloalkynes under copper catalysis. 5 mL) at room temperature for 20 min, after which time a homogeneous solution was obtained. 5 mL) and added in a single portion to the catalyst solution. The reaction mixture was stirred for 45 min, and then quenched by adding 10% NH4OH solution (1 mL).

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