Modular terpene synthesis enabled by mild electrochemical couplings
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The paper describes the development of a new methodology for constructing carbon-carbon double bonds (alkenes) in a modular and scalable way. This allows for an efficient synthesis of complex terpene natural products. The authors were inspired by nature's enzyme-catalyzed modular assembly of terpenes as well as classic synthetic approaches to these targets.
They discovered that nickel electrocatalysis coupled with silver nanoparticle-modified electrodes enables decarboxylative cross-coupling of carboxylic acids and vinyl halides. This method is mild, functional group tolerant, andGeometry controlling. The new methodology was used in concise syntheses of 13 terpenes including polyene cyclization precursors and fragrances like nerolidol. The reactions could be conducted on large scale in a flow reactor.
Mechanistic studies suggest the silver nanoparticles prevent over-reduction of the catalyst and control mass transport, explaining the efficacy of the modified electrodes. Overall, this is an important advancement in alkene synthesis, demonstrating the power of combining transition metal catalysis and electrochemistry with materials science. The new methodology enables more efficient and scalable access to complex terpenes.
https://par.nsf.gov/servlets/purl/10316753
