期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 142, 期 6, 页码 3050-3059出版社
AMER CHEMICAL SOC
DOI: 10.1021/jacs.9b12355
关键词
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资金
- University of Chicago
- NIGMS [1R01GM124414-01A1]
- CSC fellowship
- ShanghaiTech University
- National Science Foundation [ACI-1548562]
Arenes with four different contiguous substituents, i.e. 1,2,3,4-tetrasubstituted arenes, are commonly found in bioactive compounds, but they are nontrivial to access via conventional methods. Through addressing the meta constraint in the palladium/norbornene (Pd/NBE) cooperative catalysis, which is the difficulty of tolerating a sizable meta substituent in aryl halide substrates, here a modular and regioselective approach is realized for preparing 1,2,3,4-tetrasubstituted arenes. One key is the use of a C2-amide-substituted NBE, and a combined experimental and computational study reveals its role in promoting the NBE insertion and the ortho C-H metalation steps. The scope is broad: a variety of electrophiles and nucleophiles could be introduced to the ortho and ipso positions, respectively, with 1,4-disubstituted aryl halides, leading to diverse unsymmetrical contiguous tetrasubstituted arenes. Application of this approach has been demonstrated in streamlined syntheses of several bioactive compounds.
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