141503-23-3Relevant academic research and scientific papers
One-pot Synthesis of α,α-Dichloroketones from Alkynes Using the N,N-Dimethylformamide/HCl/Potassium Monoperoxysulfate System
Kim, Kye Kwang,Kim, Jae Nyoung,Kim, Kyoung Mahn,Kim, Hyoung Rae,Ryu, Eung K.
, p. 603 - 604 (1992)
The reaction of alkynes with N,N-dimethylformamide (DMF)/HCl/potassium monoperoxysulfate (Oxone, Aldrich) afforded the corresponding α,α-dichloroketones in good yields.
Dichloroacetophenone Derivatives: A Class of Bioconjugation Reagents for Disulfide Bridging
Wu, Liu-Hai,Zhou, Shuguang,Luo, Qun-Feng,Tian, Jie-Sheng,Loh, Teck-Peng
supporting information, p. 8193 - 8197 (2020/11/18)
A mild and biocompatible method for the construction of disulfide bridging in peptides using dichloroacetophenone derivatives is developed. This method is highly selective (chemo, diastereo, regio, etc.) and atom economic and works under biocompatible reaction conditions (metal-free, water, pH 7, rt, etc.).
Modular and Chemoselective Strategy for Accessing (Distinct) α,α-Dihaloketones from Weinreb Amides and Dihalomethyllithiums
Malik, Monika,Pace, Vittorio,Senatore, Raffaele,Touqeer, Saad,Urban, Ernst
supporting information, p. 5056 - 5061 (2020/10/21)
The selective transfer of diversely functionalized dihalomethyllithiums (LiCHBrCl, LiCHClI, LiCHBrI, LiCHCl2, LiCHBr2, LiCHFI) to Weinreb amides for preparing gem-dihaloketones in one synthetic operation is reported. The capability of these amides as acylating agents and, the wide availability of dihalomethanes as pronucleophiles, enable a straightforward route to the title compounds under full chemocontrol. No racemization phenomena were evidenced in the case of optically active materials. Additionally, tolerance to sensitive functional groups (esters, amides, halogens, olefins etc.) was uniformly noticed, thus making this conceptually intuitive strategy flexible and tunable by the operator. (Figure presented.).
Mild Homologation of Esters through Continuous Flow Chloroacetate Claisen Reactions
Ganiek, Maximilian A.,Ivanova, Maria V.,Martin, Benjamin,Knochel, Paul
supporting information, p. 17249 - 17253 (2018/12/05)
The selective chloromethylenation of functionalized esters using chloroacetic acid (CA) and LiHMDS (HMDS=hexamethyldisilazide) in a continuous-flow setup is reported. This Claisen homologation is for the first time extended to bis-chloromethylenation using dichloroacetic acid (DCA), thus giving access to under-explored α,α′-bis-chloroketones. The use of flow conditions enables efficient generation and reaction of the unstable chloroacetate dianion intermediates, leading to unprecedented mild and scalable reaction conditions at an economical reagent stoichiometry (?10 °C, 1 min, 1.0–2.4 equiv dianion). The clean reaction profiles allow subsequent use of the unpurified crude products, which is demonstrated in the synthesis of various heterocycles of broad interest. Furthermore, we report a novel, catalyst-free substitution of the obtained monochloro ketone products with (hetero)aryl zinc enolates to give valuable 1,4-diketones.
