Access to macrocyclic endocyclic and exocyclic allylic alcohols by nickel-catalyzed reductive cyclization of ynals.
Ni-catalyzed reductive macrocyclizations of ynals are reported. Disubstituted alkynes afford either endocyclic or exocyclic allylic alcohols depending on the ligand. Phosphine ligands favor the formation of endocyclic olefins, whereas N-heterocyclic carbene ligands favor the formation of exocyclic olefins. Terminal alkynes provide 1,2-disubstituted olefins with N-heterocyclic carbene ligands.
Knapp-Reed
Beth
B
Department of Chemistry, Wayne State University, Detroit, Michigan 48202, USA.
Mahandru
Gireesh M
GM
Montgomery
John
J
D000475:Alkenes / Q000138:chemical synthesis*; D000480:Alkynes / Q000138:chemical synthesis / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D015394:Molecular Structure; D009532:Nickel / Q000737:chemistry*; D010084:Oxidation-Reduction; D020005:Propanols / Q000138:chemical synthesis*; D013237:Stereoisomerism
D000475:Alkenes; D000480:Alkynes; D020005:Propanols; C006463:allyl alcohol; D009532:Nickel