22479-32-9Relevant academic research and scientific papers
Visible-Light-Promoted Synthesis of α-CF2H-Substituted Ketones by Radical Difluoromethylation of Enol Acetates
Cheng, Li,Dong, Bingbing,Feng, Zengqiang,Li, Yunpu,Wang, Zechao,Wu, Junliang,Zhu, Baoxiang
supporting information, p. 508 - 513 (2021/01/13)
An efficient and novel visible-light-promoted radical difluoromethylation of enol acetates for the synthesis of α-CF2H-substituted ketones has been described. Upon irradiation under blue LED with catalytic amounts of fac-Ir(ppy)3, this photocatalytic procedure employs difluoromethyltriphenylphosphonium bromide as a radical precursor. Various α-CF2H-substituted ketones are successfully created via designed systems based on the SET process. The methodology has also provided an operationally simple process with broad functional group compatibility.
Ag2CO3-mediated direct functionalization of alkyl nitriles: Facile synthesis of γ-ketonitriles through nitrile alkylation of enol acetates
Cheng, Pi,Wang, Wei,Wang, Lin,Zeng, Jianguo,Reiser, Oliver,Liang, Yun
, p. 1408 - 1412 (2019/05/06)
Direct C(sp3)-H functionalization of alkyl nitriles is a low toxic and facile route to nitrile-containing compounds. In this research, the Ag2CO3-mediated nitrile methylenation of enol acetates is developed to prepare γ-ketonitriles through the direct C(sp3)-H oxidative functionalization of acetonitrile. A radical pathway is proposed, and acetonitrile serves both as solvent and CN-containing radical source.
Formation of δ-Lactones with anti-Baeyer–Villiger Regiochemistry: Investigations into the Mechanism of the Cerium-Catalyzed Aerobic Coupling of β-Oxoesters with Enol Acetates
Geibel, Irina,Dierks, Anna,Müller, Thomas,Christoffers, Jens
, p. 7245 - 7254 (2017/05/31)
The cerium-catalyzed, aerobic coupling of β-oxoesters with enol acetates and dioxygen yields δ-lactones with a 1,4-diketone moiety. In contrast to the Baeyer–Villiger oxidation (BVO), where the higher substituted residue migrates; in the case of this oxid
Iron-Catalyzed Cross-Coupling of Alkenyl Acetates
G?rtner, Dominik,Stein, André Luiz,Grupe, Sabine,Arp, Johannes,Von Wangelin, Axel Jacobi
supporting information, p. 10545 - 10549 (2015/09/02)
Stable C-O linkages are generally unreactive in cross-coupling reactions which mostly employ more electrophilic halides or activated esters (triflates, tosylates). Acetates are cheap and easily accessible electrophiles but have not been used in cross-couplings because the strong C-O bond and high propensity to engage in unwanted acetylation and deprotonation. Reported herein is a selective iron-catalyzed cross-coupling of diverse alkenyl acetates, and it operates under mild reaction conditions (0 C, 2 h) with a ligand-free catalyst (1-2 mol%). Iron clad: Acetates are underutilized electrophiles in metal-catalyzed cross-coupling reactions because of the strong alkenyl C-O bond and their propensity to engage in unwanted reactions. Combination of a ligand-free low-valent Fe catalyst with nucleophilic organomagnesium reagents, low temperature, and short reaction times results in highly selective cross-couplings with alkenyl acetates.
Highly efficient Cu(I)-catalyzed trifluoromethylation of aryl(heteroaryl) enol acetates with CF3 radicals derived from CF3SO 2Na and TBHP at room temperature
Lu, Yang,Li, Yaming,Zhang, Rong,Jin, Kun,Duan, Chunying
, p. 128 - 133 (2014/05/06)
An efficient method for the Cu(I)-catalyzed synthesis of α-trifluoromethyl ketones via the addition of CF3 to aryl(heteroaryl) enol acetates by using the readily available CF 3SO2Na (Langlois reagent) has been developed. The reaction is experimentally simple and carried out at room temperature, providing good to excellent yields with wide functional group tolerance.
