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Mild decarboxylative allylation of coumarins.

ABSTRACT: Allyl esters of 3-carboxylcoumarins undergo facile decarboxylative coupling at just 25-50 degrees C. This represents the first extension of decarboxylative C-C bond-forming reactions to the coupling of aromatics with sp(3)-hybridized electrophiles. Finally, the same concept can be applied to the sp(2)-sp(3) couplings of pyrones and flavones. Thus, a variety of biologically important heteroaromatics can be readily functionalized without the need for strong bases or stoichiometric organometallics that are typically required for more standard cross-coupling reactions.

SUBMITTER: Jana R

PROVIDER: S-EPMC2878741 | biostudies-literature | 2009 Aug

REPOSITORIES: biostudies-literature

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Mild decarboxylative allylation of coumarins.

Jana Ranjan R Trivedi Rushi R Tunge Jon A JA

Organic letters 20090801 15

Allyl esters of 3-carboxylcoumarins undergo facile decarboxylative coupling at just 25-50 degrees C. This represents the first extension of decarboxylative C-C bond-forming reactions to the coupling of aromatics with sp(3)-hybridized electrophiles. Finally, the same concept can be applied to the sp(2)-sp(3) couplings of pyrones and flavones. Thus, a variety of biologically important heteroaromatics can be readily functionalized without the need for strong bases or stoichiometric organometallics ...[more]

PMID: 19588967

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