Synthesis and reactions of porphine-type metal complexes. 8. Carbon-carbon bond formation catalyzed by vitamin B12 and a vitamin B12 model compound. Electrosynthesis of bicyclic ketones by 1,4 addition

1980 ◽  
Vol 102 (10) ◽  
pp. 3642-3644 ◽  
Author(s):  
Rolf Scheffold ◽  
Meera Dike ◽  
Suneel Dike ◽  
Thomas Herold ◽  
Lorenz Walder
Keyword(s):  
Vitamin B12 ◽  
Metal Complexes ◽  
Model Compound ◽  
Bond Formation ◽  
Carbon Bond ◽  
Carbon Carbon Bond ◽  
Bicyclic Ketones

Carbon Dioxide-Mediated C(sp2)–H Arylation of Primary and Secondary Benzylamines

2018 ◽  
Author(s):  
Mohit Kapoor ◽  
Pratibha Chand-Thakuri ◽  
Michael Young
Keyword(s):  
Carbon Dioxide ◽  
Transition Metal ◽  
Bond Activation ◽  
Bond Formation ◽  
Carbon Bond ◽  
Chelate Effect ◽  
Free Amine ◽  
Carbon Carbon Bond ◽  
New Strategy ◽  
Metal Catalyzed

Carbon-carbon bond formation by transition metal-catalyzed C–H activation has become an important strategy to fabricate new bonds in a rapid fashion. Despite the pharmacological importance of <i>ortho</i>-arylbenzylamines, however, effective <i>ortho</i>-C–C bond formation from C–H bond activation of free primary and secondary benzylamines using Pd<sup>II</sup> remains an outstanding challenge. Presented herein is a new strategy for constructing <i>ortho</i>-arylated primary and secondary benzylamines mediated by carbon dioxide (CO<sub>2</sub>). The use of CO<sub>2</sub> is critical to allowing this transformation to proceed under milder conditions than previously reported, and that are necessary to furnish free amine products that can be directly used or elaborated without the need for deprotection. In cases where diarylation is possible, a chelate effect is demonstrated to facilitate selective monoarylation.

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