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

Ryohei Doi, Iman Abdullah, Takahisa Taniguchi, Nozomi Saito, Yoshihiro Sato

Research output: Contribution to journalArticlepeer-review

29 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)7720-7723
Number of pages4
JournalChemical Communications
Volume53
Issue number55
DOIs
Publication statusPublished - 1 Jan 2017

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