title: Functionalization of benzylic C(sp(3))-H bonds of heteroaryl aldehydes through N-heterocyclic carbene organocatalysis.
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.
authors.affiliation: Division of Chemistry & Biological Chemistry, School of Physical & Mathematical Sciences, Nanyang Technological University, Singapore 637371 (Singapore).
authors.forename: Xingkuan
authors.initials: X
authors.lastname: Chen
authors.forename: Song
authors.initials: S
authors.lastname: Yang
authors.forename: Bao-An
authors.initials: BA
authors.lastname: Song
authors.forename: Yonggui Robin
authors.initials: YR
authors.lastname: Chi
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D001593:Benzyl Compounds / Q000737:chemistry*; D002384:Catalysis; D007211:Indoles / Q000737:chemistry*; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry; D015394:Molecular Structure; D013141:Spiro Compounds
chemical_list: D000447:Aldehydes; D001593:Benzyl Compounds; D007211:Indoles; D013141:Spiro Compounds; C030011:carbene; D008697:Methane
keywords: C-H functionalization; N-heterocyclic carbenes; indoles; spiro compounds; synthetic methods