Palladium complex-catalyzed carbonylation of organic halides in the presence of cyclic ethers: Halohydrin ester synthesis

[BMIM][PF6] Promotes the Synthesis of Halohydrin Esters from Diols Using Potassium Halides

“…2. Diol could be transformed into the monoesters followed by the formation of a dioxygenated ring (7,8), similar to those proposed by several authors. 3,17,[24][25][26][27][28] These intermediates, in equilibrium with the open monoester, can tautomerize to 9.…”

“…6,7 Moreover, methodologies to synthesize these halohydrins esters are usually expensive multi-step processes. [8][9][10][11][12][13][14][15][16] In contrast, Eras et al have developed a direct methodology to the stereospecific chlorohydrin ester formation. The method consist in one-pot esterification-chlorination reaction, in which chlorotrimethylsilane acts as a solvent, catalyzer and chlorine source.…”

A Ratiometric Fluorescent Probe for Biological Signaling Molecule H2S: Fast Response and High Selectivity

“…The Pd(PPh 3 ) 4 ‐catalyzed reactions between styrene oxide and aroyl chlorides afford mixtures of chlorohydrin esters [Equation (20)],45 probably through the formation of ArCOPdCl(PPh 3 ) 2 ( 7A , Scheme ). Roloff suggested the reaction between 7A and the epoxides, as proposed by Tanaka et al,46 giving the ionic species 7B , which could evolve to the isolated compounds and the catalyst (path a ) 45. We suggest another reactive pathway, which involves a ligand exchange leading to 7C (path b ).…”

Pd‐Mediated Reactions of Epoxides

“…[44] The Pd(PPh 3 ) 4 -catalyzed reactions between styrene oxide and aroyl chlorides afford mixtures of chlorohydrin esters [Equation (20)], [45] probably through the formation of ArCOPdCl(PPh 3 ) 2 (7A, Scheme 7). Roloff suggested the reaction between 7A and the epoxides, as proposed by Tanaka et al, [46] giving the ionic species 7B, which could evolve to the isolated compounds and the catalyst (path a). [45] We suggest another reactive pathway, which involves a ligand exchange leading to 7C (path b).…”