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A general strategy for regiocontrol in nickel-catalyzed reductive couplings of aldehydes and alkynes.

ABSTRACT: 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.

SUBMITTER: Malik HA 

PROVIDER: S-EPMC2869463 | biostudies-literature | 2010 May

REPOSITORIES: biostudies-literature

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A general strategy for regiocontrol in nickel-catalyzed reductive couplings of aldehydes and alkynes.

Malik Hasnain A HA   Sormunen Grant J GJ   Montgomery John J  

Journal of the American Chemical Society 20100501 18

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 e  ...[more]

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