Studies aimed at synthesizing surfactants from biomass-based feedstocks using Pd-catalyzed telomerization of 1,3-butadiene resulted in the development of a highly active catalyst system. A ligand screening was performed, and Pd/tris(2-methoxyphenyl)phosphine (TOMPP) was identified as the most promising catalyst. A solvent- and base-free protocol was developed, which allows efficient and selective conversion of a wide variety of polyol substrates (e.g., glycerol, diols, carbohydrates, and sugar alcohols). In the case of hemi-acetal bearing sugars, catalyst deactivation was observed and mechanistic studies showed that extensive formation of ligand-derived phosphonium species depleted the amount of available ligand. Stoichiometric coordination reactions gave insight into the phosphine alkylation mechanism and demonstrated the reversibility of the observed reaction. A simple and efficient one-pot synthesis method was developed for the preparation of [Pd((1-3,7,8η)-(E)-octa-2,7-dien-1-yl)(PR3)]+ complexes, which are key reactive intermediates. Based on these studies, an extended telomerization mechanism is proposed, which accounts for the formation of ligand-derived phosphonium species and the reversibility of reaction pathways.
Pure and Applied Chemistry
The Scientific Journal of IUPAC
Ed. by Burrows, Hugh / Stohner, Jürgen
IMPACT FACTOR 2017: 5.294
CiteScore 2017: 3.42
SCImago Journal Rank (SJR) 2017: 1.212
Source Normalized Impact per Paper (SNIP) 2017: 1.546
- Online
- ISSN
- 1365-3075
Pd/TOMPP-catalyzed telomerization of 1,3-butadiene: From biomass-based substrates to new mechanistic insights
Free Access
Keywords: biomass; palladium catalysis; telomerization
Conference
International Symposium on Organometallic Chemistry Directed Towards Organic Synthesis (OMCOS-16), International Symposium on Organometallic Chemistry Directed Toward Organic Synthesis, OMCOS, Organometallic Chemistry Directed Toward Organic Synthesis, 16th, Shanghai, China, 2011-07-24–2011-07-28
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About the article
Published Online: 2012-05-24
Published in Print: 2012-05-24
Citation Information: Pure and Applied Chemistry, Volume 84, Issue 8, Pages 1713–1727, ISSN (Online) 1365-3075, ISSN (Print) 0033-4545, DOI: https://doi.org/10.1351/PAC-CON-11-12-06.
© 2013 Walter de Gruyter GmbH, Berlin/Boston.
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