Indium-mediated alkynylation of Baylis-Hillman acetates: a novel route to 1,4-enynes |
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Authors: | Jhillu S Yadav Basi V Subba Reddy Nagendra Nath Yadav Ashutosh Pratap Singh Madavi Choudhary Ajit C Kunwar |
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Institution: | Division of Organic Chemistry, Indian Institute of Chemical Technology, Hyderabad 500 007, India |
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Abstract: | Baylis-Hillman acetates undergo smooth alkynylation with aryl-susbstituted iodoalkynes in the presence of indium metal in refluxing dichloromethane to furnish 1,4-enynes in high yields with (E)-stereoselectivity. In the absence of Lewis acid, the reaction follows both SN2 and SN2′ pathways affording 1:1 mixtures of 1,4-enynes. Upon addition of 10 mol % of InBr3, the reaction proceeds preferably in the SN2′ manner. In the case of adducts derived from acrylonitrile, the corresponding products are obtained in fairly good yields and with (Z)-stereoselectivity. |
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Keywords: | Indium reagents SN2&prime substitution Allylic acetates 1 4-Enynes |
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