133464-98-9Relevant academic research and scientific papers
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.).
A Simple and Unambiguous Synthesis of α,α- and α,α'-Dihalogeno Ketones
Barluenga, Jose,Llavona, Lujan,Concellon, Jose M.,Yus, Miguel
, p. 297 - 300 (2007/10/02)
A convenient method for the unambiguous preparation of α,α'-dihalogeno ketones 3 from in situ-generated chloromethyllithium and α-chloro or α-bromo carboxylic acid esters 1 at -78 deg C, is described.The unambiguous prparation of α,α-dihalogeno ketones 7 by using in situ-generated dihalogenomethyllithium and carboxylic acid esters 5 at -78 deg C is also reported.
