TY - JOUR AU - Cabezas, Jorge A.; Poveda, Rebeca R.; Brenes, José A. TI - One-Pot Conversion of Aldehydes and Ketones into 1-Substituted and 1,4-Disubstituted 1,3-Enynes SN - 0039-7881 SN - 1437-210X PY - 2018 JO - Synthesis JF - Synthesis LA - EN VL - 50 IS - 17 SP - 3307 EP - 3321 ET - 2018/07/23 DA - 2018/08/21 KW - 1,3-dilithiopropyne KW - lithium acetylides KW - 1,3-enynes KW - palladium catalysis KW - cross-coupling KW - propargylation AB - Sequential treatment of 2,3-dichloropropene with magnesium and n-BuLi generates the operational equivalent of 1,3-dilithiopropyne, which upon treatment with aldehydes or ketones, produces the corresponding alkoxy lithium acetylide intermediates. Reaction of this alkoxide with tosyl chloride, and t-BuLi produces 1-substituted, or 1,1-disubstituted 1,3-enynes in a one-pot reaction. When this lithium acetylide intermediates, obtained by this procedure, were used to perform palladium-catalyzed cross-coupling reactions, followed by addition of thionyl chloride and pyridine, 1,4-disubstituted or 1,1,4-trisubstituted 1,3-enynes were obtained in a one-pot protocol. PB - © Georg Thieme Verlag DO - 10.1055/s-0037-1610197 UR - http://www.thieme-connect.com/products/ejournals/abstract/10.1055/s-0037-1610197 ER -