title: Cooperativity of regiochemistry control strategies in reductive couplings of propargyl alcohols and aldehydes.
abstract: The nickel-catalyzed reductive coupling of propargyl alcohols and alkynes proceeds with excellent regiochemical control with an underlying electronic preference that can be supplemented by ligand size effects. The products obtained may be readily converted to substructures that are not directly available by an aldehyde-alkyne reductive coupling. A simple model for how steric and electronic factors are both important in governing regiochemistry in couplings of this type is presented, along with examples of how the effects can combine in either a constructive or destructive manner.
authors.affiliation: Department of Chemistry, University of Michigan, Ann Arbor, Michigan 48109-1055, USA.
authors.forename: Hasnain A
authors.initials: HA
authors.lastname: Malik
authors.forename: Mani Raj
authors.initials: MR
authors.lastname: Chaulagain
authors.forename: John
authors.initials: J
authors.lastname: Montgomery
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D000480:Alkynes / Q000737:chemistry*; D002384:Catalysis; D015394:Molecular Structure; D009532:Nickel / Q000737:chemistry; D020005:Propanols / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D000480:Alkynes; D020005:Propanols; D009532:Nickel; C028255:propargyl alcohol