TY - JOUR T1 - Ligand-Controlled Diastereoselective Cobalt-Catalysed Hydroalkynylation of Terminal Alkynes to E- or Z-1,3-Enynes. AU - Weber,Sebastian M, AU - Queder,Jona, AU - Hilt,Gerhard, Y1 - 2020/09/07/ PY - 2020/04/08/received PY - 2020/4/10/pubmed PY - 2020/4/10/medline PY - 2020/4/10/entrez KW - alkynes KW - cobalt KW - enynes KW - hydroalkynylation KW - stereoselectivity SP - 12129 EP - 12133 JF - Chemistry (Weinheim an der Bergstrasse, Germany) JO - Chemistry VL - 26 IS - 53 N2 - A diastereoselective hydroalkynylation of terminal alkynes to form the head-to-head dimerization products by two different cobalt-phosphine catalyst system is reported. The use of the bidentate ligand dppp and additional triphenylphosphine led to the selective formation of the (E)-1,3-enynes (E:Z>99:1) in good to excellent yields, while the tridentate ligand TriPhos led to the corresponding (Z)-1,3-enynes in moderate to good yields with excellent stereoselectivities (up to E:Z=1:99). Both pre-catalysts are easy to handle, because of their stability under atmospheric conditions. The optimized reaction conditions were identified by the Design of Experiments (DoE) approach, which has not been used before in cobalt-catalysed reaction optimisation. DoE decreased the number of required reactions to a minimum. SN - 1521-3765 UR - https://www.unboundmedicine.com/medline/citation/32271963/Ligand_Controlled_Diastereoselective_Cobalt_Catalysed_Hydroalkynylation_of_Terminal_Alkynes_to_E__or_Z_13_Enynes_ DB - PRIME DP - Unbound Medicine ER -