Journal ArticleDOI
Flow Chemistry Syntheses of Styrenes, Unsymmetrical Stilbenes and Branched Aldehydes
Samuel L. Bourne,Matthew O'Brien,Sivarajan Kasinathan,Peter Koos,Paeivi Tolstoy,Dennis X. Hu,Roderick W. Bates,Benjamin Martin,Berthold Schenkel,Steven V. Ley +9 more
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TLDR
In this paper, a tandem flow chemistry process has been developed for the synthesis of unsymmetrical stilbenes from aryl iodides, and 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.Abstract:
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.read more
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The Hitchhiker's Guide to Flow Chemistry
TL;DR: This review introduces readers to the basic principles and fundamentals of flow chemistry and critically discusses recent flow chemistry accounts.
Dialkylbiaryl phosphines in Pd-catalyzed amination: a user's guide
TL;DR: In this paper, the selection of the best choice of reaction conditions and ligand of this class for the most commonly encountered and practically important substrate combinations for Pd-catalyzed amination reactions is discussed.
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Flow chemistry syntheses of natural products
TL;DR: This review highlights successes in the development and application of continuous flow chemistry methods for synthesis with an emphasis on new opportunities and technological advances.
Journal ArticleDOI
Organic Synthesis: March of the Machines
TL;DR: This Review focuses on the concepts, procedures and methods that have far-reaching implications in the chemistry world and their recent applications in innovative research laboratories.
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The Use of Gases in Flow Synthesis
Carl J. Mallia,Ian R. Baxendale +1 more
TL;DR: An overview of the different approaches used to introduce gases into flow reactors is presented in this article along with a synopsis of different gaseous reactions classes already successfully translated into flow and the potential benefits that can be leveraged by using flow chemistry to allow gases to be used in research in a safer and more efficient way.
References
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Journal ArticleDOI
Atom Economy—A Challenge for Organic Synthesis: Homogeneous Catalysis Leads the Way
TL;DR: The ability of transition metal complexes to preorganize π-electron systems serves as the basis both of simple additions usually accompanied by subsequent hydrogen shifts and of cycloadditions as mentioned in this paper.
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Palladium-catalyzed vinylic hydrogen substitution reactions with aryl, benzyl, and styryl halides
Richard F. Heck,J. P. Nolley +1 more
Journal ArticleDOI
Dialkylbiaryl Phosphines in Pd-Catalyzed Amination: A User's Guide.
TL;DR: Dialkylbiaryl phosphines are a valuable class of ligand for Pd-catalyzed amination reactions and have been applied in a range of contexts and this review attempts to aid the reader in the selection of the best choice of reaction conditions and ligand.