6938-44-9Relevant academic research and scientific papers
Copper-Catalyzed Alkylation of Silyl Enol Ethers with Sterically Hindered α-Bromocarbonyls: Access to the Histamine H3Receptor Antagonist
Li, Dengke
, p. 609 - 618 (2020/12/23)
A general and efficient copper-catalyzed alkylation of silyl enol ethers with functionalized alkyl bromides has been developed for the synthesis of the sterically hindered γ-ketoesters. The transformation was induced through C(sp3)-halogen activation of commercially available sterically hindered alkyl bromides under mild conditions in good results. The strategy could be used for the synthesis of biologically active histamine H3 receptor (H3R) antagonist for medicinal purposes.
Selective photoredox decarboxylation of α-ketoacids to allylic ketones and 1,4-dicarbonyl compounds dependent on cobaloxime catalysis
Zhang, Hong,Xiao, Qian,Qi, Xu-Kuan,Gao, Xue-Wang,Tong, Qing-Xiao,Zhong, Jian-Ji
, p. 12530 - 12533 (2020/11/02)
A photoredox/cobaloxime co-catalyzed coupling reaction of α-ketoacids and methacrylates to obtain allylic ketones is described. Without the cobaloxime catalyst, 1,4-dicarbonyl compounds are generated. The cobaloxime catalyst enables dehydrogenation to generate the formation of new olefins. The generality, good substrate scope and mild conditions are good features in the photoredox/cobaloxime catalysis protocol, and this method will provide new opportunities for the functionalization of more olefins.
Acyl radicals from α-keto acids using a carbonyl photocatalyst: Photoredox-catalyzed synthesis of ketones
Zhu, Da-Liang,Wu, Qi,Young, David James,Wang, Hao,Ren, Zhi-Gang,Li, Hong-Xi
supporting information, p. 6832 - 6837 (2020/10/12)
Acyl radicals have been generated from α-keto acids using inexpensive and commercially available 2-chloro-thioxanthen-9-one as the photoredox catalyst under visible light illumination. These reactive species added to olefins or coupled with aryl halides via a bipyridylstabilized Ni(II) catalyst, enabling easy access to a diverse range of ketones. This reliable, atom-economical, and eco-friendly protocol is compatible with a wide range of functional groups.
Photoredox-Catalyzed Isomerization of Highly Substituted Allylic Alcohols by C?H Bond Activation
Guo, Kai,Huang, Jun,Li, Anding,Li, Yuanhe,Yang, Zhen,Zhang, Zhongchao
, p. 11660 - 11668 (2020/05/25)
Photoredox-catalyzed isomerization of γ-carbonyl-substituted allylic alcohols to their corresponding carbonyl compounds was achieved for the first time by C?H bond activation. This catalytic redox-neutral process resulted in the synthesis of 1,4-dicarbonyl compounds. Notably, allylic alcohols bearing tetrasubstituted olefins can also be transformed into their corresponding carbonyl compounds. Density functional theory calculations show that the carbonyl group at the γ-position of allylic alcohols are beneficial to the formation of their corresponding allylic alcohol radicals with high vertical electron affinity, which contributes to the completion of the photoredox catalytic cycle.
Organic Dye-Catalyzed Intermolecular Radical Coupling of α-Bromocarbonyls with Olefins: Photocatalytic Synthesis of 1,4-Ketocarbonyls Using Air as an Oxidant
Roy Chowdhury, Soumyadeep,Singh, Deepak,Hoque, Injamam Ul,Maity, Soumitra
, p. 13939 - 13950 (2020/11/20)
An organic dye-catalyzed visible light-promoted ketocarbonylation protocol of vinyl arenes has been disclosed with the help of α-bromocarbonyls where aerial oxygen played a role of an oxidant to install the keto-oxygen functionality. This unique process i
Visible-Light-Mediated Oxidative Coupling of Vinylarenes with Bromocarboxylates Leading to γ-Ketoesters
Fang, Xing-Xiao,Wang, Peng-Fei,Yi, Wei,Chen, Wei,Lou, Sheng-Chun,Liu, Gong-Qing
, p. 15677 - 15684 (2019/12/02)
A photocatalytic strategy for the synthesis of γ-ketoesters was reported. Using DMSO as both the solvent and terminal oxidant, oxidative coupling of vinylarenes with bromocarboxylates proceeded readily, giving a variety of γ-ketoesters in good isolated yi
Visible light-induced intermolecular radical addition: Facile access to γ-ketoesters from alkyl-bromocarboxylates and enamines
Hu, Bei,Chen, Haixia,Liu, Yan,Dong, Wuheng,Ren, Kai,Xie, Xiaomin,Xu, Hao,Zhang, Zhaoguo
supporting information, p. 13547 - 13550 (2015/01/09)
A highly efficient addition of alkyl α-bromocarboxylates to enamines by visible light-induced photoredox catalysis is reported. Compared with traditional methods, the reaction described here provided an alternative route for the construction of valuable γ-ketoesters in generally good yields.
Biotransformation of aromatic ketones and ketoesters with the non-conventional yeast Pichia glucozyma
Contente, Martina Letizia,Molinari, Francesco,Zambelli, Paolo,De Vitis, Valerio,Gandolfi, Raffaella,Pinto, Andrea,Romano, Diego
supporting information, p. 7051 - 7053 (2015/02/02)
The non-conventional yeast Pichia glucozyma CBS 5766 has been used for the biotransformation of different aromatic ketones and ketoesters. The growth and biotransformation conditions were optimised for the reduction of acetophenone and under optimised conditions, propiophenone, butyrophenone and valerophenone were reduced to the corresponding (S)-alcohols with high yields and enantioselectivity. Ketoreductase(s) of Pichia glucozyma showed high catalytic activities also towards aromatic β- and γ-ketoesters, being often competitive with esterase(s). These concurrent activities allowed for the preparation of hydroxyesters, hydroxyacids and lactones often in a very selective manner.
Co-catalyzed synthesis of 1,4-dicarbonyl compounds using TBHP oxidant
Zhang, Feng,Du, Peng,Chen, Jijun,Wang, Hongxiang,Luo, Qiang,Wan, Xiaobing
supporting information, p. 1932 - 1935 (2014/05/06)
A Co-catalyzed reaction for the construction of 1,4-dicarbonyls has been reported in which cascade organocobalt addition/trapping/Kornblum-DeLaMare rearrangement were involved. In view of the easy availability of starting materials, wide substrate scope, high functionality tolerance, and operational simplicity, this protocol constituted a simple, practical, and powerful alternative compared with previous approaches.
Radical alkylations of alkyl halides and unactivated C-H bonds using vinyl triflates
Lee, Jin Young,Lim, Kyoung-Chan,Meng, Xiangjian,Kim, Sunggak
experimental part, p. 1647 - 1650 (2010/09/04)
Radical alkylations of activated alkyl iodides and bromides were achieved using vinyl triflates in the presence of hexadimethyltin, whereas those of unactivated C-H bonds using vinyl triflates proceeded cleanly under tin-free conditions. Georg Thieme Verl
