Pd-Catalyzed Dehydrogenative Oxidation of Alcohols to Functionalized Molecules

A dehydrogenative oxidation reaction of primary alcohols to aldehydes catalyzed by a simple Pd/Xantphos catalytic system was developed under an argon or nitrogen atmosphere without oxidizing agents or hydrogen acceptors. The reaction product could be easily changed: under aerobic conditions, esters...

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Bibliographic Details
Published inOrganic process research & development Vol. 23; no. 8; pp. 1709 - 1717
Main Authors Mori, Takamichi, Ishii, Chihiro, Kimura, Masanari
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 16.08.2019
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Applied
Chemistry, Organic
Physical Sciences
Science & Technology
oxidation
palladium
aldehyde
carboxylic acid
hydrogen transfer
ester
HOMOGENEOUS RUTHENIUM
CARBOXYLIC-ACID SALTS
ASTERISK-IR COMPLEX
SECONDARY ALCOHOLS
OXIDANT-FREE OXIDATION
HYDROGEN-PRODUCTION
N-ALKYLATION
ACCEPTORLESS
LIGAND
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Summary:A dehydrogenative oxidation reaction of primary alcohols to aldehydes catalyzed by a simple Pd/Xantphos catalytic system was developed under an argon or nitrogen atmosphere without oxidizing agents or hydrogen acceptors. The reaction product could be easily changed: under aerobic conditions, esters were obtained in aprotic solvents, whereas the corresponding carboxylic acids were produced in aqueous media. These oxidizing processes were applicable to the efficient synthesis of useful nitrogen-containing heterocyclic compounds such as indole, quinazoline, and benzimidazole via intramolecular versions of this reaction from amino alcohols.
ISSN:1083-6160
1520-586X
DOI:10.1021/acs.oprd.9b00207