Modular Dual-Tasked C–H Methylation via the Catellani Strategy

We report a dual-tasked methylation that is based on cooperative palladium/norbornene catalysis. Readily available (hetero)­aryl halides (39 iodides and 4 bromides) and inexpensive MeOTs or trimethylphosphate are utilized as the substrates and methylating reagent, respectively. Six types of “ipso” t...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2019-10, Vol.141 (40), p.15986-15993
Main Authors: Gao, Qianwen, Shang, Yong, Song, Fuzhen, Ye, Jinxiang, Liu, Ze-Shui, Li, Lisha, Cheng, Hong-Gang, Zhou, Qianghui
Format: Article
Language:English
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Summary:We report a dual-tasked methylation that is based on cooperative palladium/norbornene catalysis. Readily available (hetero)­aryl halides (39 iodides and 4 bromides) and inexpensive MeOTs or trimethylphosphate are utilized as the substrates and methylating reagent, respectively. Six types of “ipso” terminations can modularly couple with this “ortho” C–H methylation to constitute a versatile methylation toolbox for preparing diversified methylated arenes. This toolbox features inexpensive methyl sources, excellent functional-group tolerance, simple reaction procedures, and scalability. Importantly, it can be uneventfully extended to isotope-labeled methylation by switching to the corresponding reagents CD3OTs or 13CH3OTs. Moreover, this toolbox can be applied to late-stage modification of biorelevant substrates with complete stereoretention. We believe these salient and practical features of our dual-tasked methylation toolbox will be welcomed by academic and industrial researchers.
ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.9b07857