853063-10-2Relevant academic research and scientific papers
Ligand-Controlled Regiodivergence for Catalytic Stereoselective Semireduction of Allenamides
Hajiloo Shayegan, Mojtaba,Li, Zhong-Yuan,Cui, Xin
supporting information, (2021/12/02)
Ligand-controlled regiodivergence has been developed for catalytic semireduction of allenamides with excellent chemo- and stereocontrol. This system also provides an example of catalytic regiodivergent semireduction of allenes for the first time. The divergence of the semireduction is enabled by ligand switch with the same palladium pre-catalyst under operationally simple and mild conditions. Monodentate ligand XPhos exclusively promotes selective 1,2-semireduction to afford allylic amides, while bidentate ligand BINAP completely switched the regioselectivity to 2,3-semireduction, producing (E)-enamide derivatives.
Copper-catalysed hydroamination of N-allenylsulfonamides: The key role of ancillary coordinating groups
Blieck, Rémi,Perego, Luca Alessandro,Ciofini, Ilaria,Grimaud, Laurence,Taillefer, Marc,Monnier, Florian
supporting information, p. 1225 - 1234 (2019/02/26)
A copper-catalysed hydroamination reaction of N-allenylsulfonamides with amines has been developed through a rational approach based on mechanistic studies. The reaction is promoted by a simple copper(I) catalyst and proceeds at room temperature with complete regioselectivity and excellent stereoselectivity towards linear (E)-N-(3-aminoprop-1-enyl)sulfonamides. Density Functional Theory (DFT) studies allow interpreting the key role of unsaturated substituents on nitrogen as ancillary coordinating moieties for the copper catalyst.
A palladium-catalyzed regiocontrollable hydroarylation reaction of allenamides with B2pin2/H2O
Cui, Jie,Meng, Long,Chi, Xiaochen,Liu, Qing,Zhao, Pingping,Zhang, Dao-Peng,Chen, Lei,Li, Xinjin,Dong, Yunhui,Liu, Hui
supporting information, p. 4355 - 4358 (2019/04/26)
A novel palladium-catalyzed regiocontrollable hydroarylation reaction of allenamides with B2pin2/H2O has been disclosed. H2O as an ideal hydrogen source was activated by B2pin2 to furnish allylamines or enamines with a broad functional group tolerance. The regioselectivity for both of the two products was up to 99:1 for most of the examples, which was achieved by adjusting the addition order of the catalyst and iodobenzene derivatives. The tentative investigation of the mechanism proved the reaction to be a non-radical process and the deuterium-labeled experiments indicated that the hydrogen was from H2O.
Oxidant-dependent Cu-catalyzed alkynylation and aminomethylation: C-H versus C-C cleavage in TMEDA
Shen, Qi,Zhang, Lei,Zhou, Yu-Ren,Li, Jian-Xin
supporting information, p. 6725 - 6728 (2013/11/19)
Oxidant-dependent Cu-catalyzed alkynylation and aminomethylation reactions have been achieved under facile and mild conditions. TMEDA coupled with various terminal alkynes via C-H bond cleavage in good yields using atmospheric oxygen as an oxidant. Switching from air to TBHP afforded aminomethylation products of terminal alkynes through C-C bond cleavage of TMEDA. The protocol provided a novel strategy to prepare bi/tridentate N-ligand.
A study of (binap)(enyne)tetracarbonyldicobalt(0) complexes
Gibson, Susan E.,Hardick, David J.,Haycock, Peter R.,Kaufmann, Karina A. C.,Miyazaki, Ayako,Tozer, Matthew J.,White, Andrew J. P.
, p. 7099 - 7109 (2008/03/12)
Four (binap)(enyne)tetracarbonyldicobalt(0) complexes have been synthesised and their reactivity monitored by variable temperature 31P NMR spectroscopy. Formation of (binap)dicarbonylhydridocobalt(-1) 12 occurred at temperatures between 35 and
A study of [Co2(alkyne)(binap)(CO)4] complexes (BINAP = (1,1′-Binaphthalene)-2,2-diylbis(diphenylphosphine))
Gibson, Susan E.,Kaufmann, Karina A. C.,Loch, Jennifer A.,Steed, Jonathan W.,White, Andrew J. P.
, p. 2566 - 2576 (2007/10/03)
Understanding the interaction of chiral ligands, alkynes, and alkenes with cobaltcarbonyl sources is critical to learning more about the mechanism of the catalytic, asymmetric Pauson-Khand reaction. We have successfully characterized complexes of the type
