期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 59, 期 2, 页码 653-657出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201909557
关键词
aryl halides; C-H activation; cross-coupling; dearomatization; palladacycles
资金
- National Science Foundation of China [21672169]
- Key Science and Technology Innovation Team of Shaanxi Province [2017KCT-37]
- Education Department of Shaanxi Province [18JS108]
- Key Laboratory Project of Xian [201805058ZD9CG42]
Palladium-catalyzed alkene-directed cross-coupling of aryl iodide with another aryl halide through C-H arylation opens a unique avenue for unsymmetrical biaryl-derived molecules. However, homo-coupling of aryl iodides often erodes the overall synthetic efficiency. Reported herein is a highly chemoselective Pd-0-catalyzed alkyne-directed cross-coupling of aryl iodides with bromophenols, which was subsequently followed by phenol dearomatization to furnish a very attractive [2+2+1] spiroannulation. Notably, possible homo-coupling of aryl iodides was not observed at all. Mechanistic studies indicated that a five-membered aryl/vinyl palladacycle most likely accounts for promoting the key step of biaryl cross-coupling.
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