Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 141, Issue 40, Pages 15986-15993Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.9b07857
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Funding
- National Natural Science Foundation of China [21602161, 21871213, 21801193]
- Wuhan University
- China Postdoctoral Science Foundation [2016M602339, 2018M642894]
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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 (CH3OTs)-C-13. 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.
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