期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 21, 期 42, 页码 14703-14707出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201502101
关键词
C-H arylation; C-S bond activation; organosulfur compounds; organozinc compounds; palladium
资金
- MEXT [25107002]
- JSPS [24685007, 26620081]
- Japan Association for Chemical Innovation
- Grants-in-Aid for Scientific Research [26620081, 25107002, 24685007] Funding Source: KAKEN
C-H arylation of polyfluoroarenes and heteroarenes with aryl sulfides proceeds smoothly with the aid of a palladium-N-heterocyclic carbene catalyst. A bulky zinc amide, TMPZnCl center dot LiCl, plays a key role as an effective base to generate the corresponding arylzinc species in situ. This arylation protocol is practically much easier to perform than our previous method, which necessitates preparation of the arylzinc reagents in advance from the corresponding aryl halides. Aryl sulfides that are prepared through sulfur-specific reactions, such as SNAr sulfanylation and extended Pummerer reactions, undergo this direct arylation, offering interesting transformations that are otherwise difficult to achieve with conventional halogen-based organic synthesis.
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