54166-20-0Relevant academic research and scientific papers
Visible-Light Photoredox-Catalyzed Dicarbofunctionalization of Styrenes with Oxime Esters and CO2: Multicomponent Reactions toward Cyanocarboxylic Acids and γ-Keto Acids
Bai, Junxue,Li, Miao,Zhou, Cong,Sha, Yu,Cheng, Jiang,Sun, Jianwei,Sun, Song
, p. 9654 - 9658 (2021/12/14)
A photoredox-catalyzed dicarbofunctionalization of styrenes with oxime esters and CO2 has been achieved. Notably, a series of four-, five-, or six-membered cyclic ketone oximes worked well to furnish a wide range of ε-, ζ-, and η-cyanocarboxylic acids in good yields. Furthermore, a series of γ-keto acids also could be obtained by employing acyclic ketone oxime esters as the carbonyl radical precursor. It provides convergent access to diverse biologically important cyanocarboxylic and γ-keto acids.
Visible-Light-Promoted Selenocyanation of Cyclobutanone Oxime Esters Using Potassium Selenocyanate
Zhao, Xia,Ji, Liangshuo,Gao, Yu,Sun, Tengteng,Qiao, Jiamin,Li, Ankun,Lu, Kui
, p. 11399 - 11406 (2021/09/02)
We report the visible-light-promoted selenocyanation of cyclobutanone oxime esters using potassium selenocyanate in the presence of a fac-Ir(ppy)3 catalyst for the first time. Because of the mild conditions employed and use of readily accessible potassium selenocyanate, this method is an effective and green strategy for the synthesis of cyano and selenocyano bifunctional substituted alkanes.
Lewis Acid Catalyzed Ring-Opening Reaction of Cyclobutanones towards Conjugated Enones
Gao, Jiqiang,Guo, Ziteng,Li, Zhongjuan,Liu, Chunhui,Liu, Yu,Qiu, Tingtian,Zhang, Min,Zhao, Jinbo
, p. 6111 - 6114 (2021/12/16)
An unprecedented Fe-catalyzed ring-opening reaction of simple cyclobutanones is developed, which provides access to conjugated enones with good functional group tolerance in high yields under mild conditions. The product derivatization and gram-scale expe
Nickel-Catalyzed Favorskii-Type Rearrangement of Cyclobutanone Oxime Esters to Cyclopropanecarbonitriles
Fang, Ping,Mei, Tian-Sheng,Shuai, Bin
, p. 1637 - 1641 (2021/10/02)
A nickel-catalyzed base-promoted rearrangement of cyclobutanone oxime esters to cyclopropanecarbonitriles was developed. The ring opening of cyclobutanone oxime esters occurs at the sterically less hindered side. A base-promoted nickelacyclobutane intermediate, formed in situ, is assumed to be involved in the formation of the product.
Photocatalytic Neophyl Rearrangement and Reduction of Distal Carbon Radicals by Iminyl Radical-Mediated C?C Bond Cleavage
Yu, Xiao-Ye,Wang, Peng-Zi,Yan, Dong-Mei,Lu, Bin,Chen, Jia-Rong,Xiao, Wen-Jing
, p. 3601 - 3606 (2018/09/18)
The control of selectivity in the reactions of the highly reactive open-shell carbon radicals is an attractive but often challenging task. Building on the strategy of photoinduced iminyl radical-mediated C?C bond cleavage, we have developed photocatalytic neophyl rearrangement and reduction of distal carbon radicals under visible light irradiation of O-acyl oximes. This mild protocol tolerates a wide range of readily available O-acyl oximes, enabling facile synthesis of diversely substituted α,β-unsaturated nitriles and β-functionalized saturated nitriles in a highly selective manner. (Figure presented.).
A rhodium(I)-catalysed formal intramolecular C-C/C-H bond metathesis
Matsuda, Takanori,Yuihara, Itaru
, p. 7393 - 7396 (2015/04/27)
Phenylcyclobutanes underwent skeletal reorganisation in the presence of Wilkinson's catalyst to afford indanes through a cascade process involving chelation-assisted C-C bond cleavage and intramolecular C-H bond cleavage.
Direct syntheses of spiro- and fused-hydrofurans by a tunable tandem semipinacol rearrangement/oxa-michael addition protocol
Li, Bao-Sheng,Liu, Wen-Xing,Zhang, Qing-Wei,Wang, Shao-Hua,Zhang, Fu-Min,Zhang, Shu-Yu,Tu, Yong-Qiang,Cao, Xiao-Ping
, p. 5246 - 5249 (2013/05/22)
A highly chemoselective one-pot reaction has been developed involving a tandem semipinacol rearrangement/oxa-Michael addition sequence in which the in situ generated ketol diene intermediate can be transformed specifically to either the spiro- or fused-dihydrofuran products (see scheme). This one-pot tandem reaction represents a general synthetic methodology for the syntheses of the two different kinds of furan derivatives. Copyright
Baeyer-Villiger Oxidation of Cyclobutanones with 10-Methylacridinium as an Efficient Organocatalyst
Xu, Hua-Jian,Zhu, Feng-Fei,Shen, Yong-Ya,Wan, Xin,Feng, Yi-Si
, p. 4145 - 4151 (2012/07/27)
Baeyer-Villiger oxidation of cyclobutanones is achieved in current developed protocol with 10-methylacridinium perchlorate (AcrH +ClO4-) as a novel organocatalyst both with irradiation at room temperature and without irradiation at elevated temperature. Excellent yields of the corresponding lactones are obtained and the possible mechanism has been proposed.
Combined rhodium-catalyzed carbon-hydrogen activation and β-carbon elimination to access eight-membered rings
Crepin, Damien,Dawick, James,Aissa, Lhnstopne
supporting information; experimental part, p. 620 - 623 (2010/04/05)
(Figure Presented) Enlargel C-H bond activation and β-carbon elimination are combined in a net intramolecular hydroacylation of alkylidenecyclobutanes and alkylideneazetidines in the presence of rhodium catalysts, affording eight-membered-ring compounds in high yield (see scheme). This study demonstrates the possibility of exploiting the strain energy of azetidines through β-carbon elimination in new transition-metal-catalyzed reactions.
Palladium-catalyzed diastereo- and enantioselective Wagner-Meerwein shift: Control of absolute stereochemistry in the C-C bond migration event
Trost, Barry M.,Xie, Jia
, p. 6231 - 6242 (2008/12/20)
Inducing absolute stereochemistry in Wagner-Meerwein shifts was examined in a ring expansion protocol. Initiated by generation of a π-allylpalladium intermediate by hydropalladation of allenes, the ring expansion of allenylcyclobutanol substrates proceeded with excellent diastereo- and enantioselectivities. The results demonstrate that, during the C-C bond migration process, our chiral catalysts can control the stereochemistry of both the π-allylpalladium intermediate and the corresponding migration bond. Moreover, the stereochemical outcome of the reaction can be rationalized very well with the working model of the chiral catalyst. The method provides an efficient way to synthesize highly substituted cyclopentanones with an α-chiral O-tertiary center which has various synthetic applications.
