2867-66-5Relevant academic research and scientific papers
Reactions of organozinc reagents with potassium bromodifluoroacetate
Levin, Vitalij V.,Zemtsov, Artem A.,Struchkova, Marina I.,Dilman, Alexander D.
, p. 97 - 101 (2015)
A practical method for the synthesis of gem-difluorinated compounds from organozinc reagents is described. Potassium bromodifluoroacetate serves as a source of CF2-fragment, which is inserted into carbonzinc bond of organozinc reagents. The intermediate difluorinated organozinc species can be protonated, brominated or coupled with allylic electrophiles.
Ni-Catalyzed Formal Cross-Electrophile Coupling of Alcohols with Aryl Halides
Lin, Quan,Ma, Guobin,Gong, Hegui
, p. 14102 - 14109 (2021/11/20)
Direct coupling of unactivated alcohols remains a challenge in current synthetic chemistry. We herein demonstrate a strategy building upon in situ halogenation/reductive coupling of alcohols with aryl halides to forge Csp2-Csp3 bonds. The combination of 2-chloro-3-ethylbenzo[d]oxazol-3-ium salt (CEBO) and TBAB as the mild bromination reagents enables rapid transformation of a wide range of alcohols to their bromide counterparts within one to 5 min in CH3CN and DMF, which is compatible with the Ni-catalyzed cross-electrophile coupling conditions in the presence of a chemical reductant. The present method is suitable for arylation of a myriad of structurally complex alcohols with no need for prepreparation of alkyl halides. More importantly, the mild and kinetically rapid bromination process has shown good selectivity in the bromination/arylation of symmetric diols and less sterically hindered hydroxyl groups in polyols, thus offering promise for selective functionalization of diols and polyols without laborious protecting/deprotecting operations. The practicality of this work is also evident in the arylation of a number of carbohydrates, drug compounds, and naturally occurring alcohols.
Synthesis of Nitriles from Haloesters, Haloketones and Haloethers
Talekar, D. G.,Joshi, P. L.,Ramaiah, P.,Rao, A. S.
, p. 145 - 151 (2007/10/02)
The action of NaCN on haloesters, haloketones and haloethers has been studied.Haloesters wherein halogen and ester functions are located on adjacent carbon atoms, do not furnish the corresponding nitriles, whereas those with halogen and ester functions not located on adjacent carbon atoms, furnish the corresponding nitriles in good yields.The presence of hydroxy or ether function on the carbon adjacent to primary halide bearing carbon atom does not interfere in the reaction with cyanide. δ-Haloketones are transformed to ketonitriles, γ-Haloketones are transformed to cyclopropyl ketones and epoxyhalides to epoxynitriles.
