ChemInform Abstract: Metal-Catalyzed Activation of Ethers via C-O Bond Cleavage: A New Strategy for Molecular Diversity

ChemInform ◽  
2015 ◽  
Vol 46 (6) ◽  
pp. no-no
Author(s):  
Josep Cornella ◽  
Cayetana Zarate ◽  
Ruben Martin
Keyword(s):  
Molecular Diversity ◽  
Bond Cleavage ◽  
New Strategy ◽  
Metal Catalyzed

scholarly journals Metal-catalyzed activation of ethers via C–O bond cleavage: a new strategy for molecular diversity

2014 ◽  
Vol 43 (23) ◽  
pp. 8081-8097 ◽  
Author(s):  
Josep Cornella ◽  
Cayetana Zarate ◽  
Ruben Martin
Keyword(s):  
Molecular Diversity ◽  
Bond Activation ◽  
Aryl Halide ◽  
Bond Cleavage ◽  
Cross Coupling ◽  
New Strategy ◽  
The Cross ◽  
Metal Catalyzed

This review highlights the prospective impact of simple ethers as aryl halide surrogates in the cross-coupling arena via C–O bond-activation.

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.

Transition-Metal-Catalyzed Transformation of Sulfonates via S–O Bond Cleavage: Synthesis of Alkyl Aryl Ether and Diaryl Ether

2019 ◽  
Vol 21 (22) ◽  
pp. 8879-8883 ◽  
Author(s):  
Xuemeng Chen ◽  
Xue Xiao ◽  
Haotian Sun ◽  
Yue Li ◽  
Haolin Cao ◽  
...  
Keyword(s):  
Transition Metal ◽  
Bond Cleavage ◽  
Aryl Ether ◽  
Alkyl Aryl ◽  
Diaryl Ether ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed

Transition-Metal-Catalyzed Synthesis of Organophosphorus Compounds Involving P–P Bond Cleavage

Synthesis ◽  
2020 ◽  
Vol 52 (19) ◽  
pp. 2795-2806 ◽  
Author(s):  
Mieko Arisawa
Keyword(s):  
Transition Metal ◽  
Organophosphorus Compounds ◽  
Bond Cleavage ◽  
Palladium Complexes ◽  
Addition Reactions ◽  
Phosphonium Salts ◽  
Substitution Reactions ◽  
Sulfonic Acids ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed

Organophosphorus compounds are used as drugs, pesticides, detergents, food additives, flame retardants, synthetic reagents, and catalysts, and their efficient synthesis is an important task in organic synthesis. To synthesize novel functional organophosphorus compounds, transition-metal-catalyzed methods have been developed, which were previously considered difficult because of the strong bonding that occurs between transition metals and phosphorus. Addition reactions of triphenylphosphine and sulfonic acids to unsaturated compounds in the presence of a rhodium or palladium catalyst lead to phosphonium salts, in direct contrast to the conventional synthesis involving substitution reactions of organohalogen compounds. Rhodium and palladium complexes catalyze the cleavage of P–P bonds in diphosphines and polyphosphines and can transfer organophosphorus groups to various organic compounds. Subsequent substitution and addition reactions proceed effectively, without using a base, to provide various novel organophosphorus compounds.1 Introduction2 Transition-Metal-Catalyzed Synthesis of Phosphonium Salts by Addition Reactions of Triphenylphosphine and Sulfonic Acids3 Rhodium-Catalyzed P–P Bond Cleavage and Exchange Reactions4 Transition-Metal-Catalyzed Substitution Reactions Using Diphosphines4.1 Reactions Involving Substitution of a Phosphorus Group by P–P Bond Cleavage4.2 Related Substitution Reactions of Organophosphorus Compounds4.3 Substitution Reactions of Acid Fluorides Involving P–P Bond Cleavage of Diphosphines5 Rhodium-Catalyzed P–P Bond Cleavage and Addition Reactions6 Rhodium-Catalyzed P–P Bond Cleavage and Insertion Reactions Using Polyphosphines7 Conclusions

ChemInform Abstract: Copper-Catalyzed Aerobic Oxidative Inert C-C and C-N Bond Cleavage: A New Strategy for the Synthesis of Tertiary Amides.

ChemInform ◽  
2015 ◽  
Vol 46 (11) ◽  
pp. no-no
Author(s):  
Xiuling Chen ◽  
Tieqiao Chen ◽  
Qiang Li ◽  
Yongbo Zhou ◽  
Li-Biao Han ◽  
...  
Keyword(s):  
Bond Cleavage ◽  
New Strategy ◽  
Tertiary Amides
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