Metal-Catalyzed C-H Bond Activation and C-C Bond Formation in Water

2013 ◽  
pp. 47-86 ◽  
Author(s):  
Bin Li ◽  
Pierre H. Dixneuf
Keyword(s):  
Bond Activation ◽  
Bond Formation ◽  
Metal Catalyzed

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.

Recent Advances in Metal-Catalyzed Heterocyclic C-P Bond Formation

2020 ◽  
Vol 17 ◽  
Author(s):  
Feng Xu ◽  
Yu Hui
Keyword(s):  
Organic Synthesis ◽  
Recent Progress ◽  
Bond Activation ◽  
Low Cost ◽  
Bond Formation ◽  
Phosphorus Compounds ◽  
Catalytic Systems ◽  
Phosphorus Containing ◽  
Synthetic Pesticides ◽  
Metal Catalyzed

Abstract:: The Phosphorus-containing heterocycles are an important class of compounds in organic chemistry. Because of their potential application in many fields, especially the synthetic pesticides, medicine and catalyst, the Phosphorus-containing heterocycles have attracted continuous attention by organic synthesis scientists. The development of efficient and low-cost catalytic systems is great interest for construction heterocycles C–P bond. Usually, the Phosphorus-containing heterocycles is prepared via direct carbon–hydrogen (C–H) bond activation or pre-functionalized of heterocycles with carbon–hydrogen （ P-H） bond of phosphorus compounds reaction by metal-catalyzed. This review summarizes recent progress in the heterocycles C-P bond formation reactions by metal-catalyzed, which mainly focusing on the discussion of the reaction mechanism. Aims to provide efficient methods for the future synthesis and application in this field.

Air-stable phosphine oxides as preligands for catalytic activation reactions of C-Cl, C-F, and C-H bonds

2006 ◽  
Vol 78 (2) ◽  
pp. 209-214 ◽  
Author(s):  
Lutz Ackermann ◽  
Robert Born ◽  
Julia H. Spatz ◽  
Andreas Althammer ◽  
Christian J. Gschrei
Keyword(s):  
Bond Activation ◽  
Bond Formation ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Phosphine Oxides ◽  
Aryl Chlorides ◽  
Catalytic Activation ◽  
Cross Coupling Reactions ◽  
Palladium Catalyzed ◽  
Metal Catalyzed

Studies on the use of easily accessible heteroatom-substituted secondary phosphine oxides as preligands for cross-coupling reactions are described. These air-stable sterically hindered phosphine oxides allow for efficient palladium-catalyzed Suzuki- and nickel-catalyzed Kumada-coupling reactions using electronically deactivated aryl chlorides. In addition, they enable nickel-catalyzed coupling reactions of magnesium organyls with aryl fluorides at ambient temperature, and ruthenium-catalyzed coupling reactions of aryl chlorides via C-H bond activation. Finally, the application of modular diamino phosphine chlorides as preligands for a variety of transition-metal-catalyzed C-C and C-N bond formation reactions employing electron-rich aryl chlorides is presented.

A Review on Sulfur-Directed C−H Bond Activation

2020 ◽  
Vol 17 ◽  
Author(s):  
Xuchong Tang ◽  
Yingwei Zhao
Keyword(s):  
Transition Metal ◽  
Electron Donor ◽  
Bond Activation ◽  
Bond Formation ◽  
Metal Catalysts ◽  
Transition Metal Catalysts ◽  
Directing Group ◽  
Metal Catalyzed ◽  
Sulfur Containing

: Transition-metal-catalyzed C−H bond activation employing a directing group is becoming a powerful tool to access C−C or C−hetero bond formation. Oxygen and nitrogen atoms are commonly applied as the electron donor for these directing groups. In contrast, there are only few studies on sulfur-containing groups, probably due to their toxicity to transition-metal catalysts. Nowadays a large amount of C−H activation reactions directed by sulfur-containing auxiliary groups have been successfully achieved. Because these groups can be facilely removed or modified in situ or in further steps, they are of great value in creative synthetic strategies. This paper reviews recent advances in the studies using thioether, thiol/thiophenol/disulfide, sulfoxide, and thiocarbonyl as directing groups for intermolecular C−H functionalizations as well as intramolecular oxidative annulations.

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.

scholarly journals 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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