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Issue 55, 2017

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

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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.

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

Supplementary files

Article information


Submitted
24 Apr 2017
Accepted
22 May 2017
First published
22 May 2017

Chem. Commun., 2017,53, 7720-7723
Article type
Communication

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

R. Doi, I. Abdullah, T. Taniguchi, N. Saito and Y. Sato, Chem. Commun., 2017, 53, 7720 DOI: 10.1039/C7CC03127K

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