603110-65-2Relevant academic research and scientific papers
Rhodium(iii)-catalyzed diamidation of olefins: Via amidorhodation and further amidation
Wang, Jinlei,Zheng, Guangfan,Li, Xingwei
supporting information, p. 7809 - 7812 (2020/07/27)
Rh(iii)-catalyzed synthesis of vicinal diamides has been realized via elaboration of an authenticated Rh-C(sp3) species generated via initial intramolecular amidorhodation of olefins. The second amidation was achieved using both electrophilic and nucleophilic amidating reagents. The reactions proceeded under mild conditions with good yield, broad substrate scope, and excellent functional-group tolerance.
Copper-mediated/catalyzed oxyalkylation of alkenes with alkylnitriles
Bunescu, Ala,Wang, Qian,Zhu, Jieping
, p. 14633 - 14636 (2015/01/09)
A copper-promoted oxyalkylation of alkenes with alkylnitriles has been developed. The protocol provides rapid access to phthalides (γ-lactones) or isochromanones (d-lactones) via the formation of a C(sp3)-C(sp3) and a C(sp3)-O bond with the generation of up to two quaternary carbon atoms. Mechanistic studies suggest that this reaction is initiated by the formation of the C(sp3)-C(sp3) bond rather than the C(sp3)-O bond. Catalytic conditions were subsequently developed using carboxylic acid as an internal nucleophile.
C3-symmetric cinchonine-squaramide-catalyzed asymmetric chlorolactonization of styrene-type carboxylic acids with 1,3-dichloro-5,5- dimethylhydantoin: An efficient method to chiral isochroman-1-ones
Han, Xin,Dong, Chune,Zhou, Hai-Bing
supporting information, p. 1275 - 1280 (2014/05/06)
A more practical and efficient catalytic asymmetric chlorolactonization of styrene-type carboxylic acids with 1,3-dichloro-5,5-dimethylhydantoin (DCDMH) using C3-symmetric cinchonine-squaramide (CSCS) as organocatalyst has been developed. A series of chiral chloro-substituted isochroman-1-ones was obtained in excellent yields (up to 95%) and enantioselectivities (up to 99% ee), whwereby the results for chloro-substituted isochroman-1-ones are the best ever achieved. The catalyst can be recovered and reused for six cycles. Moreover, the chlorolactonization product 3b was further transformed to optically active bicyclic isochroman-1-one derivatives in high yield without losing the enantioselectivity. Furthermore, compounds 3e and 2n proved to be highly potent inhibitors of the HIV-1 in TZM-bl cells.
Pd-Catalyzed intramolecular oxyalkynylation of alkenes with hypervalent iodine
Nicolal, Stefano,Erard, Stephane,Gonzalez, Davinla Fernandez,Waser, Jerome
supporting information; experimental part, p. 384 - 387 (2010/03/04)
(Figure presented) The first example of intramolecular oxyalkynylation of nonactivated alkenes using oxidative Pd chemistry is reported. Both phenol and aromatic or aliphatic acid derivatives could be used under operator-friendly conditions (room temperature, technical solvents, under air). The discovery of the superiority of benzlodoxolone-derlved hypervalent iodine reagent 3d as an alkyne transfer reagent further expands the rapidly increasing utility of hypervalent iodine reagents in catalysis and is expected to have important implications for other similar processes.
Oxidative cyclizations in a nonpolar solvent using molecular oxygen and studies on the stereochemistry of oxypalladation
Trend, Raissa M.,Ramtohul, Yeeman K.,Stoltz, Brian M.
, p. 17778 - 17788 (2007/10/03)
Oxidative cyclizations of a variety of heteroatom nucleophiles onto unactivated olefins are catalyzed by palladium(II) and pyridine in the presence of molecular oxygen as the sole stoichiometric oxidant in a nonpolar solvent (toluene). Reactivity studies of a number of N-ligated palladium complexes show that chelating ligands slow the reaction. Nearly identical conditions are applicable to five different types of nucleophiles: phenols, primary alcohols, carboxylic acids, a vinylogous acid, and amides. Electronrich phenols are excellent substrates, and multiple olefin substitution patterns are tolerated. Primary alcohols undergo oxidative cyclization without significant oxidation to the aldehyde, a fact that illustrates the range of reactivity available from various Pd(II) salts under differing conditions. Alcohols can form both fused and spirocyclic ring systems, depending on the position of the olefin relative to the tethered alcohol; the same is true of the acid derivatives. The racemic conditions served as a platform for the development of an enantioselective reaction. Experiments with stereospecifically deuterated primary alcohol substrates rule out a "Wacker-type" mechanism involving anti oxypalladation and suggest that the reaction proceeds by syn oxypalladation for both mono- and bidentate ligands. In contrast, cyclizations of deuterium-labeled carboxylic acid substrates undergo anti oxypalladation.
