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The Thiol-yne reaction (also alkyne hydrothiolation) is an organic reaction between a thiol and an alkyne. The reaction product is an alkenyl sulfide. The reaction was first reported in 1949 with thioacetic acid as reagent and rediscovered in 2009 It is used in click chemistry and in polymerization, especially with dendrimers. This addition reaction is typically facilitated by a radical initiator or UV irradiation and proceeds through a sulfanyl radical species.With monoaddition a mixture of E/Z alkenes form. The mode of addition is anti-Markovnikov. The radical intermediate can engage in secondary reactions such as cyclisation. With diaddition the 1,2-disulfide or the 1,1- dithioacetal forms. Reported catalysts for radical additions are triethylborane, indium(III) bromide and AIBN. The reaction is also reported to be catalysed by cationic rhodium and iridium complexes, by thorium and uranium complexes, by rhodium complexes, by caesium carbonate and by gold. Diphenyl disulphide reacts with alkynes to a 1,2-bis(phenylthio)ethylene. Reported alkynes are ynamides ==Polymer chemistry== In polymer chemistry, systems have been described based on addition polymerisation with 1,4-benzenedithiol and 1,4-diethynylbenzene, in the synthesis of dendrimers,〔 in star polymers,〔''Thiol–yne ‘click’ chemistry as a route to functional lipid mimetics'' Sandeep S. Naik, Justin W. Chan, Christopher Comer, Charles E. Hoyle and Daniel A. Savin Polym. Chem., 2011, 〕〔''Luminescent Hyperbranched Polymers: Combining Thiol-Yne Chemistry with Gold-Mediated C−H Bond Activation'' Dominik Konkolewicz, Sylvain Gaillard, Andrew G. West, Yuen Yap Cheng, Angus Gray-Weale, Timothy W. Schmidt, Steven P. Nolan, and Sbastien Perrier Organometallics, Article ASAP 〕〔''Stimuli-responsive star polymers through thiol–yne core functionalization/crosslinking of block copolymer micelles'' 〕 in graft polymerisation, block copolymers 〔''Hyperbranched alternating block copolymers using thiol–yne chemistry: materials with tuneable properties'' Dominik Konkolewicz, Cheuk Ka Poon, Angus Gray-Weale and Sébastien Perrier Chem. Commun., 2010〕 and in polymer networks.〔 Another reported application is the synthesis of macrocycles via dithiol coupling.〔''Synthesis of Sulfuric Macrocycles and a Rotaxane through Thiol-yne Click and Dithiol Coupling Reactions'' Weidong Zhou, Haiyan Zheng, Yongjun Li, Huibiao Liu and Yuliang Li 2010 Org. Lett. 〕 抄文引用元・出典: フリー百科事典『 ウィキペディア（Wikipedia）』 ■ウィキペディアで「Thiol-yne reaction」の詳細全文を読む スポンサード リンク
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