Nickel‐Catalyzed Domino Heck‐Type Reactions Using Methyl Esters as Cross‐Coupling Electrophiles

Autor:	Stephen G. Newman, Yan-Long Zheng
Rok vydání:	2019
Předmět:	Substitution reaction 010405 organic chemistry Chemistry Hydride chemistry.chemical_element Homogeneous catalysis General Medicine General Chemistry 010402 general chemistry 01 natural sciences Medicinal chemistry Catalysis 0104 chemical sciences Acylation Nickel Nucleophile Electrophile
Zdroj:	Angewandte Chemie International Edition. 58:18159-18164
ISSN:	1521-3773 1433-7851
DOI:	10.1002/anie.201911372
Popis:	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.
Databáze:	OpenAIRE
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