Solvent-free telomerization of isoprene with alcohols catalyzed by palladium(ɪɪ) carbene complexes

Topchiy, Maxim A.; Ageshina, Alexandra A.; Rzhevskiy, Sergey A.; Minaeva, Lidiya I.; Nechaev, Mikhail S.; Asachenko, Andrey F.

doi:10.1007/s11172-022-3494-2

Cited by 7 publications

(1 citation statement)

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“…After the successful reaction with butadiene 1a , the more challenging diene isoprene 1b was also tested under the reaction conditions in Table . The results (Table S2) show that for all the Pd-phosphine catalysts tested, the desired aryl-coupled telomerization products 3b and 4b were found as major products (∼90%), and the only minor product found was 6 (∼10%).…”

Section: Resultsmentioning

confidence: 99%

Diverted Telomerization Reaction with Aryl Boronic Derivatives: Expeditious Synthesis of Aryl-Substituted 1,6- and 1,7-dienes

Lerma-Berlanga,

Cerón-Carrasco,

Leyva-Pérez

2024

Organometallics

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The telomerization reaction is a fundamental transformation in industry for the synthesis of highly substituted medium linear carbon chain products (8−12 carbon atoms) with heteroatoms (typically oxygen and nitrogen atoms). Here we show that this multibond forming reaction can be interrupted by adding an aryl boronic derivative in the reaction mixture, which diverts the reaction pathway from the final heteroatom toward the aryl coupling to give aryl-substituted 1,6-and 1,7-dienes in a very simple manner. Carbon chains between 14 and 30 carbon atoms can be prepared. Experimental and computational studies support a reaction mechanism that combines the classical telomerization reaction during the first steps and the Tsuji−Trost reaction for the last steps. These results open the way to designing different telomerization reactions where the final coupled fragment is not a canonical nucleophile.

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Section: Resultsmentioning

confidence: 99%