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- Title
Nickel‐Catalyzed Domino Heck‐Type Reactions Using Methyl Esters as Cross‐Coupling Electrophiles.
- Authors
Zheng, Yan‐Long; Newman, Stephen G.
- Abstract
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 °C. With the σ‐NiII intermediate generated from the insertion of acyl NiII 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.
- Subjects
METHYL formate; ELECTROPHILES; HECK reaction; COUPLING reactions (Chemistry); NUCLEOPHILES; ESTERS; INFANTS
- Publication
Angewandte Chemie, 2019, Vol 131, Issue 50, p18327
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201911372