期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 138, 期 32, 页码 10132-10135出版社
AMER CHEMICAL SOC
DOI: 10.1021/jacs.6b06908
关键词
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资金
- MEXT [26708011]
- MEXT (JSPS KAKENHI) [JP16H01005]
- CREST, JST
- Japan Society for the Promotion of Science [26-04342]
- Grants-in-Aid for Scientific Research [26708011, 14F04342, 16H01005, 15H05754] Funding Source: KAKEN
Iron-catalyzed C-H functionalization of aromatics has attracted widespread attention, from chemists in recent years, while the requirenien( of an elaborate directing group on the substrate has so far hampered the use of simple aromatic carbonyl compounds such as benzoic acid and ketones, much reducing its synthetic utility. We describe here a combination of a mildly reactive' methylaluminum reagent and a new tridentate phosphine ligand for metal catalysis, 4-(bis(2-(diphenylphosphanyl)phenyl)phosphany1)-N,N-dimethyl- aniline (Me2N-TP), that allows us to convert an ortho C H bond to a C-CH3 bond in aromatics and heteroaromatics bearing simple carbonyl groups under mild oxidative conditions. The reaction is powerful enough to methylate all four ortho C-H bonds in benzophenone. The reaction tolerates a variety of functional groups, such as boronic ester, halide, sulfide, heterocycles, and enolizable ketones.
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