Telomerization of 1,3-butadiene with various alcohols by Pd/TOMPP catalysts: new opportunities for catalytic biomass valorization

Abstract

The telomerization of 1,3-butadiene with various alcohols has been investigated using a catalyst based on a Pd(acac)₂ precursor and a phosphine ligand, TOMPP (TOMPP = tris-(o-methoxyphenyl)phosphine). We were able to demonstrate the capability of the catalyst to telomerize 1,3-butadiene with various multifunctional nucleophiles having primary and secondary alcohol functions. High yields of telomer products (>98%) were obtained in very short reaction times (<2 h). The telomerization activity and selectivity of the Pd/TOMPP complex was strongly influenced by the type of alcohol used as substrate. When diols were used, telomerization of 1,3-butadiene with 1,2-propanediol and 1,2-butanediol afforded the highest yield of mono-telomer (over 70%) and for 1,2-butanediol a turnover frequency (TOF) of 300 000 h⁻¹ was reached, combined with a turnover number (TON) of 7800.