Functionalization of Benzylic C(sp3)H Bonds of Heteroaryl Aldehydes through N-Heterocyclic Carbene Organocatalysis

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...

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Veröffentlicht in:	Angewandte Chemie International Edition 2013-10, Vol.52 (42), p.11134-11137
Hauptverfasser:	Chen, Xingkuan, Yang, Song, Song, Bao-An, Chi, Yonggui Robin
Format:	Artikel
Sprache:	eng
Schlagworte:	Aldehydes - chemistry Benzyl Compounds - chemistry C-H functionalization Catalysis indoles Indoles - chemistry Methane - analogs & derivatives Methane - chemistry Molecular Structure N-heterocyclic carbenes Spiro Compounds synthetic methods
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Beschreibung
Zusammenfassung:	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.
ISSN:	1433-7851 1521-3773
DOI:	10.1002/anie.201305861