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Synthesis of 3‐Arylated 3,4‐Dihydrocoumarins: Combining Continuous Flow Hydrogenation with Laccase‐Catalysed Oxidation
Author(s) -
Suljić Sanel,
Pietruszka Jörg
Publication year - 2014
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201300990
Subject(s) - laccase , chemistry , knoevenagel condensation , flow chemistry , yield (engineering) , organic chemistry , combinatorial chemistry , catalysis , enzyme , materials science , metallurgy
A convenient arylation of diverse 3,4‐dihydrocoumarins with a number of catechols is described leading to a new class of compounds. As key step, a laccase‐catalysed oxidation/Michael addition sequence is applied using commercially available laccase from Agaricus bisporus . 3,4‐Dihydrocoumarins were obtained in a rapid and facile two‐step sequence starting from salicylaldehydes: The corresponding coumarins were synthesised through a Knoevenagel condensation in up to 83% yield followed by a quantitative reduction performed in a flow system. Combining the reductive flow reaction with the laccase‐catalysed arylation also led to successful consecutive one‐pot approaches. Overall, the enzyme‐catalysed arylations were carried out with yields ranging from 63 to 94%.