358349-85-6Relevant academic research and scientific papers
Ester Formation via Nickel-Catalyzed Reductive Coupling of Alkyl Halides with Chloroformates
Zheng, Min,Xue, Weichao,Xue, Teng,Gong, Hegui
supporting information, p. 6152 - 6155 (2016/12/09)
The synthesis of alkyl esters from readily available alkyl halides and chloroformates was achieved for the first time using a mild Ni-catalyzed reductive coupling protocol. Unactivated primary and secondary alkyl iodides as well as glycosyl, benzyl, and aminomethyl halides were successfully employed to yield products in moderate to excellent yields with high functional group tolerance.
Ligand exchange reaction of sulfoxides in organic synthesis: A versatile procedure for one-carbon homologation of methylesters to esters, thioesters, carboxylic acids and amides
Satoh, Tsuyoshi,Unno, Hideaki,Mizu, Yasuhiro,Hayashi, Yasumasa
, p. 7843 - 7854 (2007/10/03)
A novel two-step procedure for one-carbon homologation of methylesters to esters, thioesters, carboxylic acids and amides is described. Methylesters are reacted with lithium carbanion of chloromethyl phenyl sulfoxide to give α-chloro α-sulfinyl ketones in 70 to 90% yields. Potassium enolate of the α-chloro α-sulfinyl ketone was treated with tert-butyllithium at -78°C to give alkynolate via alkylidene carbenoid. This intermediate was treated with alcohols, thioles, 5% aqueous NaOH, and amine hydrochlorides to afford one-carbon homologated esters, thioesters, carboxylic acids and amides, respectively, in good to excellent yields.
