Nickel-Catalyzed Cross-Electrophile Coupling with Organic Reductants in Non-Amide Solvents.
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.
Department of Chemistry, University of Rochester, Rochester, NY, 14627-0216, USA.
Lukiana L
LL
Anka-Lufford
Department of Chemistry, University of Rochester, Rochester, NY, 14627-0216, USA.
Kierra M M
KM
Huihui
Department of Chemistry, University of Rochester, Rochester, NY, 14627-0216, USA.
Nicholas J
NJ
Gower
Department of Chemistry, University of Rochester, Rochester, NY, 14627-0216, USA.
Laura K G
LK
Ackerman
Department of Chemistry, University of Rochester, Rochester, NY, 14627-0216, USA. daniel.weix@rochester.edu.
Daniel J
http://orcid.org/0000-0002-9552-3378
DJ
Weix
cross-coupling; green chemistry; heterocycles; homogeneous catalysis; nickel