期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 22, 期 33, 页码 11564-11567出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201602668
关键词
cross-coupling; green chemistry; heterocycles; homogeneous catalysis; nickel
资金
- ACS GCI Pharmaceutical Roundtable Research Grant
- Pfizer
- Novartis
Cross-electrophile coupling of aryl halides with alkyl halides has thus far been primarily conducted with stoichiometric metallic reductants in amide solvents. This report demonstrates that the use of tetrakis(dimethylamino) ethylene (TDAE) as an organic reductant enables the use of non-amide solvents, such as acetonitrile or propylene oxide, for the coupling of benzyl chlorides and alkyl iodides with aryl halides. Furthermore, these conditions work for several electron-poor heterocycles that are easily reduced by manganese. Finally, we demonstrate that TDAE addition can be used as a control element to 'hold' a reaction without diminishing yield or catalyst activity.
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