Nickel-catalyzed hydrocarboxylation of ynamides with CO2 and H2O: observation of unexpected regioselectivity.

Abstract

We describe the nickel-catalyzed hydrocarboxylation of ynamides with CO2 and H2O to afford a variety of α-amino-α,β-unsaturated esters with high regioselectivities. The selective α-carboxylation of ynamides with this catalytic protocol is unexpected in view of the electronic bias of ynamides and is in sharp contrast to our previous study in which a stoichiometric amount of Ni(0) was used to form a β-carboxylated product exclusively. We revealed that this unexpected C-C bond formation was induced by the combination of Zn and MgBr2.

DOI: 10.1039/c7cc03127k

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Cite this paper

@article{Doi2017NickelcatalyzedHO, title={Nickel-catalyzed hydrocarboxylation of ynamides with CO2 and H2O: observation of unexpected regioselectivity.}, author={Ryohei Doi and Iman Abdullah and Takahisa Taniguchi and Nozomi Saito and Yoshihiro Sato}, journal={Chemical communications}, year={2017}, volume={53 55}, pages={7720-7723} }