Metallophthalocyanine complex, Cr(TBPC)OTf: an efficient, recyclable Lewis acid catalyst in the regio- and stereoselective rearrangement of epoxides to aldehydes

Abstract

The metallophthalocyanine complex Cr(TBPC)OTf works as a highly efficient, recyclable Lewis acid catalyst for the regio- and stereoselective rearrangements of epoxides to aldehydes.

Catalytic, regioselective, and green methods for rearrangement of 1,2-diaryl epoxides to carbonyl compounds employing metallic triflates, Brønsted-acidic ionic liquids (ILs), and IL/microwave; experimental and computational substituent effect study on aryl versus hydrogen migration

“…These reactions typically employed DCM, THF, MeCN, and Et 2 O as solvent. A high-valent metalloporphyrin complex Cr(TPP)OTf in DCE solvent proved efficient in regio-and stereo-selective epoxide rearrangement to aldehydes [15,16].…”

“…These reactions typically employed DCM, THF, MeCN, and Et 2 O as solvent. A high-valent metalloporphyrin complex Cr(TPP)OTf in DCE solvent proved efficient in regio-and stereo-selective epoxide rearrangement to aldehydes [15,16].Despite the significantly greater migratory aptitude of hydrogen versus aryl, a large majority of Lewis acid-catalyzed epoxide ring opening reactions of styrene oxides and stilbene oxides result in the formation of aldehydes (aryl migration) (Fig. 1), but situations where the ketone is formed, either as minor product along with the aldehyde or as a major product, have also been reported [5].…”

Ruthenium (II) sulfoxides-catalyzed hydrogenolysis of glycols and epoxides

“…carbonyl compounds (Scheme 3). Existing precedents [19][20][21][38][39][40][41][42][43][44] and our initial findings suggest that two cyclic pathways (I and II) are viable, as shown in Scheme 3. We suggest the hydrogenative loss of one chloride ligand to generate L 4 RuHCl + HCl and the initial reaction proceeds through an ionic mechanism.…”

Ethyl 2-[1,3-dioxo-6-(piperidin-1-yl)-2,3-dihydro-1H-benz[de]isoquinolin-2-yl]acetate

“…For general structural and background information on phthalocyanines, including properties and appplications, see: Kobayashi (2001); LukCentyanets (1999); Suda et al (2009);Zhang et al (2009). For the synthesis of the title compound, see: del Rey et al (1998).…”