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Flow Chemistry Syntheses of Styrenes, Unsymmetrical Stilbenes and Branched Aldehydes
Author(s) -
Bourne Samuel L.,
O'Brien Matthew,
Kasinathan Sivarajan,
Koos Peter,
Tolstoy Päivi,
Hu Dennis X.,
Bates Roderick W.,
Martin Benjamin,
Schenkel Berthold,
Ley Steven V.
Publication year - 2013
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.201200778
Subject(s) - hydroformylation , chemistry , flow chemistry , heck reaction , aryl , styrene , separator (oil production) , rhodium , syngas , organic chemistry , catalysis , palladium , microreactor , copolymer , alkyl , polymer , physics , thermodynamics
Two tandem flow chemistry processes have been developed. A single palladium‐catalysed Heck reaction with ethylene gas provides an efficient synthesis for functionalised styrenes. Through further elaboration the catalyst becomes multi‐functional and performs a second Heck reaction providing a single continuous process for the synthesis of unsymmetrical stilbenes. In addition, the continuous, rhodium‐catalysed, hydroformylation of styrene derivatives with syngas affords branched aldehydes with good selectivity. Incorporation of an in‐line aqueous wash and liquid–liquid separation allowed for the ethylene Heck reaction to be telescoped into the hydroformylation step such that a single flow synthesis of branched aldehydes directly from aryl iodides was achieved. The tube‐in‐tube semi‐permeable membrane‐based gas reactor and liquid–liquid separator both play an essential role in enabling these telescoped flow processes.