Hydroformylation of recalcitrating biorenewable compounds containing trisubstituted double bonds

• Published in: Applied catalysis. A, General General, 2020-02, Vol.591, p.117406, Article 117406
• Main Authors: Faria, Amanda de Camargo, de Oliveira, Mileny P., Monteiro, Amanda C., Mota, Rayssa L.V., Oliveira, Kelley C.B., Santos, Eduardo N. dos, Gusevskaya, Elena V.
• Format: Article
• Language: English
• Subjects: Alkenes; Biorenewables; Chemical bonds; Hydroformylation; Limonene; Oxidation; Rhodium; Selectivity; Substrates; Terpineol; α-Ionone
• ISSN: 0926-860X; 1873-3875
• DOI: 10.1016/j.apcata.2019.117406

[Display omitted] •Hydroformylation of challenging natural alkenes with trissubstituted double bonds.•α-Terpineol, terpinen-4-ol and α-ionone give carbonylated products in high yields.•Unprecedented yields of dialdehydes through the double hydroformylation of limonene.•Eco-friendly solvents - anisole, diethylcarbonate and p-cymene - can replace toluene.•The methods developed represent attractive entries to new fragrant compounds. Hydroformylation is a useful tool in industrial organic syntheses and it is easily applied to substrates containing terminal CC double bonds. Applying this reaction to substrates containing other functionalities or trisubstituted CC double bonds is not straightforward. Herein, the hydroformylation of several biorenewable alkenes with these features, namely: α-terpineol, terpinen-4-ol, limonene (double hydroformylation), and α-ionone, is presented. Only by the judicious choice of the catalytic system and reaction conditions, was it possible to obtain good yields and selectivity for these substrates.