A general strategy for regiocontrol in nickel-catalyzed reductive couplings of aldehydes and alkynes.
A strategy for catalyst-controlled regioselectivity in aldehyde-alkyne reductive couplings has been developed. This strategy is the first where either regiochemical outcome may be selected for a broad range of couplings, without relying on substrate biases or directing effects. The complementary use of small cyclopropenylidene carbene ligands or highly hindered N-heterocyclic carbene ligands allows the regiochemical reversal with unbiased internal alkynes, aromatic internal alkynes, conjugated enynes, or terminal alkynes.
Malik
Hasnain A
HA
Department of Chemistry, University of Michigan, Ann Arbor, Michigan 48109-1055, USA.
Sormunen
Grant J
GJ
Montgomery
John
J
D000447:Aldehydes / Q000737:chemistry*; D000480:Alkynes / Q000737:chemistry*; D002384:Catalysis; D008024:Ligands; D008697:Methane / Q000031:analogs & derivatives / Q000737:chemistry; D009532:Nickel / Q000737:chemistry*; D010084:Oxidation-Reduction; D013237:Stereoisomerism; D013379:Substrate Specificity
D000447:Aldehydes; D000480:Alkynes; D008024:Ligands; C030011:carbene; D009532:Nickel; D008697:Methane
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