Pincer Carbene Enables Nitrile Coupling

Pincer Carbene Enables Nitrile Coupling

Pincer carbene ligands mediate the coupling of a coordinated acetonitrile ligand and its unusual reactivity opens application in catalysis

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A Short, Gram-Scale Synthesis of 2,5-Disubstituted Furans

A Short, Gram-Scale Synthesis of 2,5-Disubstituted Furans (pages 3219–3222)
Stanley Chang, Saheena Desai, Daniel B. Leznoff, Nabyl Merbouh and Robert Britton
 | DOI: 10.1002/ejoc.201300305

European Journal of Organic Chemistry

A modified Feist–Bénary furan synthesis has been developed that involves a lithium aldol reaction of an -chloroaldehyde followed by a thermally induced tetrahydrofuran formation/dehydration sequence. This process provides access to a range of 2,5-disubstituted furans and is demonstrated on multigram scale.

A modified Feist–Bénary furan synthesis has been developed that involves a lithium aldol reaction between a methyl ketone and an α-chloroaldehyde followed by a thermally induced tetrahydrofuran formation/dehydration sequence and affords 2,5-disubstituted furans in good overall yield. This process is demonstrated on multigram scale and is amenable to the production of symmetric or asymmetric furans that incorporate a range of substituents (e.g., aryl, tert-butyl, ferrocenyl).

http://onlinelibrary.wiley.com/doi/10.1002/ejoc.201300305/abstract