期刊
ADVANCED SYNTHESIS & CATALYSIS
卷 362, 期 3, 页码 679-687出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201901383
关键词
carboxytelomerisation; palladium; carbonylation; homogeneous catalysis; esters
资金
- Fonds der Chemischen Industrie
- Max Planck Society
Palladium catalysed carboxytelomerisation of 1,3-butadiene with alcohols yields unsaturated C-9-pelargonic esters in an atom-economic and straightforward way. Although carboxytelomerisation is of current interest, limitations of applicable alcohol substrates have not been fully investigated. In here, we present the transfer of the catalytic system comprising palladium acetate and tri-n-butyl phosphine in pyridine to a broad variety of 20 alcohols with vast difference in nucleophilicity and sterical demands yielding the corresponding esters in a 100% atom economic manner. Effects of nucleophilicity and sterical demands were revealed for monoalcohols, di- and polyols. Whilst yields, chemoselectivity and E/Z-selectivity of the pelargonic acid derivatives were excellent with up to 99%, selectivity towards mono-, di- and triesters could be controlled successfully. Finally, the reaction profile of the carboxytelomerisation glycerol was uncovered, yielding up to 97% of industrially relevant unsaturated C-9-short chain fats.
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