Iron catalysed cross-couplings of azetidines – application to the formal synthesis of a pharmacologically active molecule

2015 ◽  
Vol 51 (11) ◽  
pp. 2111-2113 ◽  
Author(s):  
Dixit Parmar ◽  
Lena Henkel ◽  
Josef Dib ◽  
Magnus Rueping
Keyword(s):  
Cross Coupling ◽  
Grignard Reagents ◽  
Active Molecule ◽  
Formal Synthesis ◽  
Iron Catalysis ◽  
The Cross ◽  
Pharmacologically Active

A protocol for the cross-coupling of azetidines with aryl, heteroaryl, vinyl and alkyl Grignard reagents has been developed under iron catalysis. In addition, a short formal synthesis of a pharmacologically active molecule was demonstrated.

scholarly journals Iron-Catalyzed C(sp2)–C(sp3) Cross-Coupling of Aryl Chlorobenzoates with Alkyl Grignard Reagents

Molecules ◽  
2020 ◽  
Vol 25 (1) ◽  
pp. 230 ◽  
Author(s):  
Elwira Bisz ◽  
Michal Szostak
Keyword(s):  
Organic Synthesis ◽  
Nucleophilic Addition ◽  
Functional Group ◽  
High Selectivity ◽  
Cross Coupling ◽  
Environmentally Benign ◽  
Grignard Reagents ◽  
High Importance ◽  
Iron Salts ◽  
The Cross

Aryl benzoates are compounds of high importance in organic synthesis. Herein, we report the iron-catalyzed C(sp2)–C(sp3) Kumada cross-coupling of aryl chlorobenzoates with alkyl Grignard reagents. The method is characterized by the use of environmentally benign and sustainable iron salts for cross-coupling in the catalytic system, employing benign urea ligands in the place of reprotoxic NMP (NMP = N-methyl-2-pyrrolidone). It is notable that high selectivity for the cross-coupling is achieved in the presence of hydrolytically-labile and prone to nucleophilic addition phenolic ester C(acyl)–O bonds. The reaction provides access to alkyl-functionalized aryl benzoates. The examination of various O-coordinating ligands demonstrates the high activity of urea ligands in promoting the cross-coupling versus nucleophilic addition to the ester C(acyl)–O bond. The method showcases the functional group tolerance of iron-catalyzed Kumada cross-couplings.

ChemInform Abstract: Nickel-Butadiene Catalytic System for the Cross-Coupling of Bromoalkanoic Acids with Alkyl Grignard Reagents: A Practical and Versatile Method for Preparing Fatty Acids.

ChemInform ◽  
2013 ◽  
Vol 44 (28) ◽  
pp. no-no
Author(s):  
Takanori Iwasaki ◽  
Kiyokazu Higashikawa ◽  
Vutukuri P. Reddy ◽  
Willbe W. S. Ho ◽  
Yukari Fujimoto ◽  
...  
Keyword(s):  
Fatty Acids ◽  
Catalytic System ◽  
Cross Coupling ◽  
Grignard Reagents ◽  
The Cross

Highly Active [Pd(μ-Cl)(Cl)(NHC)]2(NHC = N-Heterocyclic Carbene) in the Cross-Coupling of Grignard Reagents with Aryl Chlorides

2009 ◽  
Vol 28 (9) ◽  
pp. 2915-2919 ◽  
Author(s):  
Caroline E. Hartmann ◽  
Steven P. Nolan ◽  
Catherine S. J. Cazin
Keyword(s):  
Cross Coupling ◽  
Grignard Reagents ◽  
Aryl Chlorides ◽  
Highly Active ◽  
The Cross
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