Premium
Ligand‐Controlled Diastereoselective Cobalt‐Catalysed Hydroalkynylation of Terminal Alkynes to E ‐ or Z ‐1,3‐Enynes
Author(s) -
Weber Sebastian M.,
Queder Jona,
Hilt Gerhard
Publication year - 2020
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202001697
Subject(s) - terminal (telecommunication) , cobalt , ligand (biochemistry) , chemistry , stereochemistry , medicinal chemistry , combinatorial chemistry , computer science , organic chemistry , computer network , receptor , biochemistry
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.