184370-65-8Relevant academic research and scientific papers
N -Alkynyl Pyrrole Based Total Synthesis of Shensongine A
Kerwin, Sean M.,Reinus, Brandon J.
, p. 4085 - 4105 (2019/10/28)
A copper-catalyzed N-alkynylation of pyrrole and a gold-catalyzed spiroketalization were key steps in the total synthesis of the pyrrole spiroketal alkaloid shensongine A. The preparation of this alkaloid is concise and amenable to the rapid synthesis of
Nickel-catalyzed hydrocarboxylation of ynamides with CO2 and H2O: Observation of unexpected regioselectivity
Doi, Ryohei,Abdullah, Iman,Taniguchi, Takahisa,Saito, Nozomi,Sato, Yoshihiro
, p. 7720 - 7723 (2017/07/15)
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.
Efficient synthesis of monosubstituted 3-alkynylfurans via Suzuki coupling
Yang, Xiaobao,Zhu, Li,Zhou, Yuedong,Li, Zhong,Zhai, Hongbin
, p. 1729 - 1732 (2008/12/22)
A convenient synthesis of monosubstituted 3-alkynyl-furans by Suzuki coupling reaction of 3-furanylboronic acid with substituted acetylene bromides is described. The internal alkyne products were attainable in 50-89% yields from substrates free of relatively acidic protons. Our protocol is expected to find applications in the synthesis of structurally related natural products.
Palladium-catalysed hydrostannylations of 1-bromoalkynes. A practical synthesis of (E)-1-stannylalk-1-enes
Boden, Christopher D. J.,Pattenden, Gerald,Ye, Tao
, p. 2417 - 2419 (2007/10/03)
A practical synthesis of (E)-1-stannylalk-1-enes containing a range of oxygen and nitrogen functionality is highlighted, involving hydrostannylation followed by palladium-catalysed carbon-bromine bond cleavage reactions of 1-bromoalkynes.
