Journal
MOLBANK
Volume 2023, Issue 1, Pages -Publisher
MDPI
DOI: 10.3390/M1586
Keywords
homogeneous catalysis; carbonylation; bis-alkoxycarbonylation; palladium; aryl alpha-diimine ligand; succinic acid ester; succinates
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The synthesis of dibenzyl-(1S*,2S*)-2,3-dihydro-1H-indene-1,2-dicarboxylate is achieved by a diastereospecific bis-alkoxycarbonylation reaction using 1H-indene, benzyl alcohol, and carbon monoxide. The catalyst is formed in situ by mixing Pd(TFA)(2), the ligand N-2,N-3-bis(2,6-dimethylphenyl)butane-2,3-diimine, and p-benzoquinone as the oxidant.
The synthesis of dibenzyl-(1S*,2S*)-2,3-dihydro-1H-indene-1,2-dicarboxylate has been realized through a diastereospecific bis-alkoxycarbonylation reaction, which starts from the cheap and easily available 1H-indene, benzyl alcohol, and carbon monoxide. The catalyst is formed in situ by mixing Pd(TFA)(2), the ligand N-2,N-3-bis(2,6-dimethylphenyl)butane-2,3-diimine, p-benzoquinone is used as an oxidant, and benzyl alcohol acts both as a nucleophile and as the main solvent.
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