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

作者:Doi Ryohei; Abdullah Iman; Taniguchi Takahisa; Saito Nozomi; Sato Yoshihiro*
来源:Chemical communications, 2017, 53(55): 7720-7723.
DOI:10.1039/c7cc03127k

摘要

We describe the nickel-catalyzed hydrocarboxylation of ynamides with CO2 and H2O to afford a variety of alpha-amino-alpha, beta-unsaturated esters with high regioselectivities. The selective alpha-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 beta-carboxylated product exclusively. We revealed that this unexpected C-C bond formation was induced by the combination of Zn and MgBr2.

  • 出版日期2017-7-14