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20.2.4.2.14 Dibutyl Hexanedioate by Dicarbonylation of Buta-1,3-diene

DOI: 10.1055/sos-SD-120-00173

Yang, Z.; Dong, K.Science of Synthesis Knowledge Updatesearly view.

Despite the developments in homogeneous catalytic carbonylation in the past 80 years, several aims were still to be achieved. Among them, the direct dicarbonylation of buta-1,3-diene to afford an adipate (hexanedioate) represents one of the most salient challenges. This process is a superior alternative to the nitric acid mediated oxidation of cyclohexanone, which requires an anti-corrosive reaction vessel and produces stoichiometric amounts of nitrous oxide (N2O). Beller and co-workers have presented a method for the palladium-catalyzed dicarbonylation of buta-1,3-diene that provides dialkyl adipates. The key to success is the choice of the ligand; the use of bidentate phosphine ligands featuring basic pyridyl substituents on phosphorus proved essential for high activity (e.g., ligand 26). By this protocol, the dialkoxycarbonylation of buta-1,3-diene with butan-1-ol led to the direct synthesis of adipate diesters (e.g., 27) in high yield and selectivity (Scheme 14).[‌18‌]

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