Haloalkyne Chemistry by Huanfeng Jiang, Chuanle Zhu, Wanqing Wu

By Huanfeng Jiang, Chuanle Zhu, Wanqing Wu

This publication provides effective and sensible equipment for the synthesis of assorted functionalized natural molecules from haloalkynes via varied response methods reminiscent of cross-coupling reactions, nucleophilic additions and cycloadditions. It comprises 4 chapters demonstrating attention-grabbing examples of those modifications, and showcasing the bogus strength of haloalkynes for fast meeting of complicated molecular buildings. many of the protocols let a number of bond-forming occasions to take place in one operation, providing possibilities to increase chemical synthesis and handle the expanding calls for for eco-friendly and sustainable chemistry. It additionally offers a variety of functionalized items, together with many synthetically priceless conjugated cyclic and acyclic constructions that experience strength functions in fabrics technological know-how, chemical biology and ordinary product synthesis. This publication is a priceless reference not just for natural chemists, but additionally for biologists and fabrics scientists concerned about the fashionable synthesis of natural compounds and fabrics.

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Initially, the bromoalkyne intermediate was formed through the Ag-promoted bromination of terminal alkynes. 36 Proposed mechanism R1 H F Br R1 + AgOH Ag2O AgL F AgL Br R1 I R1 H R1 AgL + H I m H2O 35 Ag (Ag ) H2O Br AgF R1 R1 Br AgL 34 R1 Br Br AgL AgL 33 transferred to the corresponding vinylsilver intermediate 35 by trans-addition of AgF to bromoalkyne. Finally, protonation of 35 afforded the final product and silver oxide. The high regio- and stereoselectivities were proposed to be originated from the back-side attack of the fluoride anion (34 to 35) as well as the bromide atom was regarded as both an activating and regio-directing functional group.

One of the most effective methods to access these compounds is the hydrothiolation of haloalkynes. In 2014, Zhu’s group documented a K2CO3-promoted hydrothiolation reaction of haloalkynes, producing β-halo alkenyl sulfides in high yields with excellent regio- and stereoselectivities. 45) [189]. 5 mmol). After stirring at room temperature for 10 h, the reaction mixture was quenched with water, extracted with EtOAc, dried over Na2SO4 and concentrated. Column chromatography on silica gel gave the βhalo alkenyl sulfide products.

Notably, this reaction was highly chemoselective, and the key to obtain satisfactory yields was the slow addition of the Grignard reagents to the reaction mixture. 20). 20 Copper-catalyzed cross-coupling of Grignard reagents with haloalkynes 28 3 Reactions of Haloalkynes General Procedure for Copper-Catalyzed Cross-Coupling of Grignard Reagents with Haloalkynes: A dry and nitrogen flushed four-necked flask (100 mL) equipped with a mechanical stirrer, a thermometer, a nitrogen inlet, and a septum was charged with CuCl2 (3 mol%), N-methylpyrrolidinone (4 mol%), haloalkyne (10 mmol), and THF (9 mL).

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