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Angewandte Chemie (International ed. in English)

Functionalization of benzylic C(sp(3))-H bonds of heteroaryl aldehydes through N-heterocyclic carbene organocatalysis.


PMID 24038663

Abstract

Aryl aldehyde activation: Oxidative activation of 2-methylindole-3-carboxaldehyde (I) through N-heterocyclic carbene (NHC) organocatalysis generates heterocyclic ortho-quinodimethane (II) as a key intermediate. This intermediate then undergoes formal [4+2] cycloaddition with trifluoromethyl ketones or isatins to form polycyclic lactones containing a quaternary carbon center.

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262439
2-Methylindole-3-carboxaldehyde, 97%
C10H9NO