New reusable heterogeneous catalyst in the MPV reduction in cyclohexenones: moderate one-pot synthesis of cyclohexenols (effect of methyl substituents)

• Published in: Journal of the Iranian Chemical Society Vol. 20; no. 1; pp. 29 - 36
• Main Author: Uysal Karatas, Burcu
• Format: Journal Article
• Language: English
• Published: Berlin/Heidelberg Springer Berlin Heidelberg 01.01.2023; Springer Nature B.V
• Subjects: Analytical Chemistry; Biochemistry; Catalysts; Chemical reduction; Chemical synthesis; Chemistry; Chemistry and Materials Science; Inorganic Chemistry; Inorganic compounds; Organic Chemistry; Original Paper; Physical Chemistry; Recyclability; Steric hindrance; Substitutes; Cyclohexenols; Heterogeneous catalysis; Pr; Cyclohexenones; MCM-41; MPV reaction; In(O
• ISSN: 1735-207X; 1735-2428
• DOI: 10.1007/s13738-022-02698-2

Inorganic compounds grafted MCM-41 catalysts and the Meerwein–Ponndorf–Verley reduction (MPV) on these heterogeneous catalysts are very attractive subject areas in chemistry. New mesoporous In(O i Pr) 3 -MCM-41 was tested for MPV reaction of cyclohexenones. Effect of methyl substituents on cyclohexenol yield was investigated. Also, reusability of catalyst was studied. Mesoporous In(O i Pr) 3 -MCM-41 catalyzed MPV reduction in cyclohexenones to corresponding cyclohexenols in pretty good yields. Higher reaction times and lower alcohol yields for the methyl substitute cyclohexenones were obtained with In(O i Pr) 3 -MCM-41 compared with the non-sübstitute cyclohexenone. Methyl substitute cyclohexenones as compared with non-substitute cyclohexenone compounds have lower activities that probably resulted from steric hindrance of alkyl group. Methyl group can create steric effect for cite accessibility of the catalyst. Moreover, In(O i Pr) 3 -MCM-41 catalyst exhibited excellent recyclability for six MPV reduction round without significant loss of the reactivity. Also, the In(O i Pr) 3 does not leach during the reduction reaction. Heterogeneous In(O i Pr) 3 -MCM-41 was found as very influential catalyst for the preparation of cyclohexenol derivatives.