57900-02-4Relevant academic research and scientific papers
Activation of mononuclear arene ruthenium complexes for catalytic propargylation directly with propargyl alcohols
Bustelo, Emilio,Dixneuf, Pierreh H.
, p. 933 - 942 (2007)
Mononuclear complexes of the type [(p-cymene)RuX(CO)(PR3)][OTf] (R = Ph, Cy; X = Cl, OTf) promote the direct catalytic propargylation of furan with propargyl alcohols. These precursors are generated in situ from [(p-cymene)RuCl(OTf)(PR3)] by activation of the propargylic alcohol, leading to the carbonyl ligand formation via allenylidene and alkenyl-hydroxycarbene intermediates. The generation of the catalytically active species requires a short initial thermal activation to induce decoordination of the p-cymene ligand. The in situ generated catalyst has been applied to catalytic transformations of alkynes and propargylic alcohols: propargylation of furans, propargyl ether synthesis from internal and terminal propargylic alcohols with propargyl, homopropargyl and allyl alcohols, selective dimerization of phenylacetylene into E-enyne, and propargyl alcohol rearrangement into α,β-unsaturated aldehydes and ketones via the Meyer-Schuster rearrangement. The propargylation of propargylic alcohols containing internal C≡C bonds suggests an activation via the Nicholas-type intermediate, the metalstabilized propargyl cation.
Gold(I)-catalyzed decarboxylation of propargyl carbonates: Reactivity reversal of the gold catalyst from π-Lewis acidity to σ-Lewis acidity
Shen, Ruwei,Yang, Jianjun,Zhu, Shugao,Chen, Chao,Wu, Luling
, p. 1259 - 1269 (2015/04/22)
A cationic gold(I)-catalyzed decarboxylative etherification of propargyl carbonates to selectively produce propargyl ethers is reported. In the reaction the gold(I) catalyst shows a distinct σ-Lewis acidity rather than the commonly observed π-Lewis acidity, and thus catalyzes the decarboxylation of a variety of propargyl carbonates to give the corresponding propargyl ethers with high selectivity. This reaction represents a rare example of the tunable reactivity of cationic gold(I) complexes between σ-Lewis acidity and π-Lewis acidity.
Mo(CO)6-mediated intramolecular pauson-Khand reaction of substituted Diethyl 3-Allyloxy-1-Propynylphosphonates
Moradov, Dorit,Quntar, Abed Al Aziz Al,Youssef, Manar,Smoum, Reem,Rubinstein, Abraham,Srebnik, Morris
supporting information; experimental part, p. 1029 - 1033 (2009/08/08)
Cyclisation of diethyl 3-allyloxy-1-propynylphosphonates with Mo(CO) 6 under PK conditions to give 3-substituted-5-oxo-3,5,6,6a- tetrahydro-1H-cyclopenta[c]furan-4-ylphosphonate, 2a-h,in45-88% isolated yields was done. The R groups are always syn with Hb (where applicable). The stereochemistry was determined via both NMR and crystal X-ray analysis.
PtCh-catalyzed tandem triple migration reaction toward (Z)-1,5-dien-2-yl esters
Ji, Ke-Gong,Shu, Xing-Zhong,Chen, Jin,Zhao, Shu-Chun,Zheng, Zhao-Jing,Lu, Li,Liu, Xue-Yuan,Liang, Yong-Min
supporting information; experimental part, p. 3919 - 3922 (2009/05/31)
(Figure Presented) A novel method for the selective synthesis of (Z)-1,5-dien-2-yl esters has been developed though Pt(II)-catalyzed tandem 1,2-acyl and 1,2-hydride migration, along with an allyl migration reaction of propargylic carboxylates with electro
Palladium-catalyzed silastannation of secondary propargylic alcohols and their derivatives
Nielsen, Thomas E.,Le Quement, Sebastian Le,Tanner, David
, p. 1381 - 1390 (2007/10/03)
A series of terminal propargylic alcohols and their derivatives were subjected to Pd-catalyzed silastannation. In all reactions, complete regio- and stereoselectivities were observed with the tributyltin moiety exclusively adding to the internal carbon of the triple bond in a cis fashion, including the first example of a diyne bis-silastannation. Silastannation reaction products could sequentially be protiodesilylated or iododestannylated, thus providing synthetic routes to 1,1-gem-disubstituted alkenylstannanes and iodides, respectively.
