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Palladium Catalyzed meta-C-H Functionalization of Masked Aromatic Aldehydes
Marcus E Farmer1, Peng Wang1, Hang Shi1
1Department of Chemistry, The Scripps Research Institute, 10550 N. Torrey Pines Road, La Jolla, California 92037.
Abstract:
Palladium catalyzed meta-C-H functionalization enabled by transient mediators has the potential to extend the utility of directed ortho-C-H functionalization to remote positions. However, there have been no reports of palladium catalyzed meta-C-H functionalization of aromatic aldehyde derivatives, which are highly versatile intermediates in organic synthesis. Herein we report the development of a directing group that, in the presence of a norbornene derived mediator and an appropriate pyridone ligand, allows palladium catalyzed meta-C-H functionalization of masked aromatic aldehydes. Mechanistic insight regarding the impact of the directing group length on this catalysis is also discussed.
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