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Palladium Catalyzed meta-C-H Functionalization of Masked Aromatic Aldehydes.

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.

SUBMITTER: Farmer ME

PROVIDER: S-EPMC6301045 | biostudies-literature | 2018 Aug

REPOSITORIES: biostudies-literature

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Palladium Catalyzed meta-C-H Functionalization of Masked Aromatic Aldehydes.

Farmer Marcus E ME Wang Peng P Shi Hang H Yu Jin-Quan JQ

ACS catalysis 20180705 8

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 a ...[more]

PMID: 30581651

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