Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 58, Issue 50, Pages 18159-18164Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201911372
Keywords
esters; cross-coupling; cyclizations; homogeneous catalysis; nickel
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Funding
- BASF
- National Science and Engineering Research Council of Canada (NSERC)
- Canada Research Chair program
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While esters are frequently used as traditional electrophiles in substitution chemistry, their application in cross-coupling chemistry is still in its infancy. This work demonstrates that methyl esters can be used as coupling electrophiles in Ni-catalyzed Heck-type reactions through the challenging cleavage of the C(acyl)-O bond under relatively mild reaction conditions at either 80 or 100 degrees C. With the sigma-Ni-II intermediate generated from the insertion of acyl Ni-II species into the tethered C=C bond, carbonyl-retentive products were formed by domino Heck/Suzuki-Miyaura coupling and Heck/reduction pathways when organoboron and mild hydride nucleophiles are used.
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