Ruthenium-Catalyzed Oxidative Cyanation of Tertiary Amines with Molecular Oxygen or Hydrogen Peroxide and Sodium Cyanide: sp3C−H Bond Activation and Carbon−Carbon Bond Formation

2008 ◽  
Vol 130 (33) ◽  
pp. 11005-11012 ◽  
Author(s):  
Shun-Ichi Murahashi ◽  
Takahiro Nakae ◽  
Hiroyuki Terai ◽  
Naruyoshi Komiya
Keyword(s):  
Hydrogen Peroxide ◽  
Molecular Oxygen ◽  
Bond Activation ◽  
Bond Formation ◽  
Sodium Cyanide ◽  
Tertiary Amines ◽  
Carbon Bond ◽  
Carbon Carbon Bond

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.

Aerobic Photooxidative Carbon–Carbon Bond Formation Between Tertiary Amines and Carbon Nucleophiles Using 2-Chloroanthra-9,10-quinone

Synlett ◽  
2014 ◽  
Vol 25 (10) ◽  
pp. 1453-1457 ◽  
Author(s):  
Akichika Itoh ◽  
Tomoaki Yamaguchi ◽  
Tomoya Nobuta ◽  
Norihiro Tada ◽  
Tsuyoshi Miura ◽  
...  
Keyword(s):  
Bond Formation ◽  
Tertiary Amines ◽  
Carbon Bond ◽  
Carbon Nucleophiles ◽  
Carbon Carbon Bond
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