Ionic liquids in Barbier-Zaitsev reaction. Synthesis of 1-(perfluorophenyl)-2-phenylethanol in the presence of iron pentacarbonyl

Abstract

The addition of benzyl bromide to pentafluorobenzaldehyde promoted by metal complex systems underlain by Fe(CO) 5 in the presence of a molar amount of ionic liquid led to the formation of 1-(perfluorophenyl)-2-phenylethanol in up to 60% yield.

Alkylation of Cymantrene with 1-Bromoadamantane Initiated by Iron Pentacarbonyl

“…The plausible mechanism of alkylation includes the formation of an intermediate complex of Fe(CO) 5 with bromoadamantane that activates alkyl halide [25] and gives rise to a radical, as it was assumed earlier [6][7][8]. The reaction conditions explored are likely to facilitate the formation of a sterically hindered radical or radical ion [26,27].…”

“…Unlike the previously reported example of alkylation of aromatic compounds with bulky adamantyl fragment [10], in our case the relative content of dialkylated products were high. This example open new opportunities for the application of iron pentacarbonyl as an initiator for different С-С bond forming reactions involving not only aliphatic [1][2][3][4][5][6][7][8] and aromatic [9] derivatives, but also organometallic compounds.…”

“…The ability of iron pentacarbonyl to initiate a range of С-С bond forming reactions is well known [1][2][3][4][5][6][7][8][9]. Iron pentacarbonyl (Fe(CO) 5 ) was shown to promote the addition of αhalocarboxylic acid esters and nitriles to aldehydes and ketones by the Reformatsky-type reaction [1][2][3].…”

“…Iron pentacarbonyl (Fe(CO) 5 ) was shown to promote the addition of αhalocarboxylic acid esters and nitriles to aldehydes and ketones by the Reformatsky-type reaction [1][2][3]. It was used successfully in diastereoselective hydrodimerization of aromatic aldehydes leading to diols [4], stereoselective reductive dimerization of chiral α-bromoamides resulting in bis(amides) [5], and addition of С 4 F 9 I to pentafluorobenzaldehyde [6] and benzyl bromide by the Zaitsev-Barbier reaction [7,8].…”