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. 2009 Aug 6;11(15):3434-6.
doi: 10.1021/ol901288r.

Mild decarboxylative allylation of coumarins

Ranjan Jana  1 , Rushi Trivedi, Jon A Tunge
Affiliations

Mild decarboxylative allylation of coumarins

Ranjan Jana et al. Org Lett. .

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.

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Figures

Figure 1
Figure 1
Biologically active 3-alkyl coumarins.
Scheme 1
Scheme 1
Scheme 2
Scheme 2
Scheme 3
Scheme 3
Decarboxylative Coupling/Heck Reaction
See this image and copyright information in PMC

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