71095-26-6Relevant academic research and scientific papers
α-Oxocarboxylic Acids as Three-Carbon Insertion Units for Palladium-Catalyzed Decarboxylative Cascade Synthesis of Diverse Fused Heteropolycycles
Zhou, Liwei,Qiao, Shujia,Zhou, Fengru,Xuchen, Xinyu,Deng, Guobo,Yang, Yuan,Liang, Yun
supporting information, p. 2878 - 2883 (2021/05/05)
A novel palladium-catalyzed decarboxylative cascade cyclization for the assembly of diverse fused heteropolycycles by employing α-oxocarboxylic acids as three-carbon insertion units is reported. This protocol enables the synthesis of isoquinolinedione- and indolo[2,1-a]isoquinolinone-fused benzocycloheptanones in moderate to good yields by the use of different aryl iodides, including alkene-tethered 2-iodobenzamides and 2-(2-iodophenyl)-1H-indoles. Notably, the approach achieves simultaneous construction of both six- and seven-membered rings via sequential intramolecular carbopalladation, C-H activation, and decarboxylation.
Atmosphere-Controlled Palladium-Catalyzed Divergent Decarboxylative Cyclization of 2-Iodobiphenyls and α-Oxocarboxylic Acids
Zhou, Liwei,Sun, Mingjie,Zhou, Fengru,Deng, Guobo,Yang, Yuan,Liang, Yun
supporting information, p. 7150 - 7155 (2021/09/18)
A novel palladium-catalyzed divergent decarboxylative cyclization of 2-iodobiphenyls and α-oxocarboxylic acids utilizing the atmosphere as a controlled switch is reported. Under the protection of a nitrogen atmosphere, tribenzotropones are synthesized by a [4 + 3] decarboxylative cyclization. Employing a palladium/O2 system enables a [4 + 2] decarboxylative cyclization to assemble triphenylenes. Notably, preliminary mechanistic studies indicate that the formation of triphenylenes involves a double decarboxylation.
Asymmetric Synthesis and Application of Chiral Spirosilabiindanes
Chang, Xin,Chen, Hong-Chao,Li, Chuan-Ying,Ma, Pei-Long,Wang, Peng
supporting information, p. 8937 - 8940 (2020/04/30)
Reported here is the development of a class of chiral spirosilabiindane scaffolds by Rh-catalyzed asymmetric double hydrosilation, for the first time. Enantiopure SPSiOL (spirosilabiindane diol), a new type of chiral building block for the preparation of various chiral ligands and catalysts, was readily prepared on greater than 10 gram scale using this protocol. The potential of this new spirosilabiindane scaffold in asymmetric catalysis was preliminarily demonstrated by development of the corresponding monodentate phosphoramidite ligands (SPSiPhos), which were used in both a Rh-catalyzed hydrogenation and a Pd-catalyzed intramolecular carboamination.
Metal-free visible light-promoted synthesis of isothiazoles: A catalytic approach for N-S bond formation from iminyl radicals under batch and flow conditions
Alemán, José,Berton, Mateo,Cabrera-Afonso, María Jesús,Cembellín, Sara,Halima-Salem, Adnane,Maestro, M. Carmen,Marzo, Leyre,Miloudi, Abdellah
supporting information, p. 6792 - 6797 (2020/11/09)
A sustainable synthesis of isothiazoles has been developed using an α-amino-oxy acid auxiliary and applying photoredox catalysis. This simple strategy features mild conditions, broad scope and wide functional group tolerance representing a new enviromenta
PdII-Catalyzed Oxidative Tandem aza-Wacker/Heck Cyclization for the Construction of Fused 5,6-Bicyclic N,O-Heterocycles
Ye, Chenghao,Kou, Xuezhen,Xia, Jingzhao,Yang, Guoqiang,Kong, Li,Wei, Quhao,Zhang, Wanbin
supporting information, p. 1897 - 1901 (2018/07/31)
A PdII-catalyzed oxidative tandem cyclization was developed for the construction of fused 5,6-bicyclic N, O-heterocycles. This reaction was enabled by the combined use of a 3-methylpyridine ligand and pentafluorobenzoic acid additive. A range of heterocyclic products with different substituents could be prepared in moderate to good yields via this methodology. Several transformations, including a scaled-up preparation of product 2 a, were also carried out showing the good applicability of our methodology.
One-Pot Asymmetric Synthesis of Alkylidene 1-Alkylindan-1-ols Using Br?nsted Acid and Palladium Catalysis
Faggyas, Réka J.,Calder, Ewen D. D.,Wilson, Claire,Sutherland, Andrew
, p. 11585 - 11593 (2017/11/10)
A one-pot catalytic enantioselective allylboration/Mizoroki-Heck reaction of 2-bromoaryl ketones has been developed for the asymmetric synthesis of 3-methyleneindanes bearing a tertiary alcohol center. Br?nsted acid-catalyzed allylboration with a chiral BINOL derivative was followed by a palladium-catalyzed Mizoroki-Heck cyclization, resulting in selective formation of the exo-alkene. This novel protocol provides a concise and scalable approach to 1-alkyl-3-methyleneindan-1-ols in high enantiomeric ratios (up to 96:4 er). The potential of these compounds as chiral building blocks was demonstrated with efficient transformation to optically active diol and amino alcohol scaffolds.
Preparation of isoindolinones via a palladium-catalyzed diamination
Li, Yu,Kou, Xuezhen,Ye, Chenghao,Zhang, Xinghua,Yang, Guoqiang,Zhang, Wanbin
supporting information, p. 285 - 288 (2017/01/03)
A Pd(II)-catalyzed cyclization using oxidative olefin diamination was developed for the preparation of isoindolinones from ortho-olefinic N-methoxybenzamides. Using the optimized reaction conditions, the desired products were obtained in up to 90% yield using NFSI as the oxidant. This reaction provides an efficient and direct access to isoindolinones with amine functionality, an important drug skeleton.
Nucleophile promoted gold redox catalysis with diazonium salts: C-Br, C-S and C-P bond formation through catalytic Sandmeyer coupling
Peng, Haihui,Cai, Rong,Xu, Chang,Chen, Hao,Shi, Xiaodong
, p. 6190 - 6196 (2016/09/03)
Gold-catalyzed C-heteroatom (C-X) coupling reactions are evaluated without using sacrificial oxidants. Vital to the success of this methodology is the nucleophile-assisted activation of aryldiazonium salts, which could be an effective oxidant for converting Au(i) to Au(iii) even without the addition of an assisting ligand or photocatalyst. By accelerating the reaction kinetics to outcompete C-C homo-coupling or diazonium dediazoniation, gold-catalyzed Sandmeyer reactions were achieved with different nucleophiles, forming C-Br, C-S and C-P bonds in high yields and selectivities.
Palladium-Catalyzed Aerobic Aminooxygenation of Alkenes for Preparation of Isoindolinones
Kou, Xuezhen,Li, Yu,Wu, Liang,Zhang, Xinghua,Yang, Guoqiang,Zhang, Wanbin
supporting information, p. 5566 - 5569 (2015/12/01)
A palladium-catalyzed intramolecular isoindolinone-forming aminooxygenation of alkenes with 1 atm of oxygen as oxidant is reported. A variety of functionalized alkenes and carboxylic acids can be used, and high yields were observed. Preliminary mechanistic studies revealed that the aminooxygenation products were formed through the oxidation of a C-PdII species using a strong oxidant, peroxide, which is generated in situ from a Pd(OAc)2/bpy/O2/HOAc catalytic system.
Facile synthesis of 1-naphthols through a copper-catalyzed arylation of methyl ketones with o-bromoacetophenones
Lou, Zhen-Bang,Pang, Xin-Long,Chen, Chao,Wen, Li-Rong,Li, Ming
supporting information, p. 1231 - 1235 (2015/12/30)
The coupling reactions of simple methyl ketones with o-bromoacetophenones and subsquential cyclization reactions were realized to produce a range of 1-naphthols. These cascade reactions were initiated by a rare Cu-catalyzed arylation reaction of methyl ketones with aromatic bromides.
