C−C Bond Formation via C−H Bond Activation Using an in Situ-Generated Ruthenium Catalyst

2009 ◽  
Vol 131 (22) ◽  
pp. 7887-7895 ◽  
Author(s):  
Rémi Martinez ◽  
Marc-Olivier Simon ◽  
Reynald Chevalier ◽  
Cyrielle Pautigny ◽  
Jean-Pierre Genet ◽  
...  
Keyword(s):  
Bond Activation ◽  
Bond Formation ◽  
Ruthenium Catalyst

ChemInform Abstract: C-C Bond Formation via C-H Bond Activation Using an in situ Generated Ruthenium Catalyst.

ChemInform ◽  
2009 ◽  
Vol 40 (44) ◽  
Author(s):  
Remi Martinez ◽  
Marc-Olivier Simon ◽  
Reynald Chevalier ◽  
Cyrielle Pautigny ◽  
Jean-Pierre Genet ◽  
...  
Keyword(s):  
Bond Activation ◽  
Bond Formation ◽  
Ruthenium Catalyst

A Versatile Ruthenium Catalyst for CC Bond Formation by CH Bond Activation

2006 ◽  
Vol 45 (48) ◽  
pp. 8232-8235 ◽  
Author(s):  
Rémi Martinez ◽  
Reynald Chevalier ◽  
Sylvain Darses ◽  
Jean-Pierre Genet
Keyword(s):  
Bond Activation ◽  
Bond Formation ◽  
Ruthenium Catalyst

A Versatile Ruthenium Catalyst for C—C Bond Formation by C—H Bond Activation.

ChemInform ◽  
2007 ◽  
Vol 38 (14) ◽  
Author(s):  
Remi Martinez ◽  
Reynald Chavalier ◽  
Sylvain Darses ◽  
Jean-Pierre Genet
Keyword(s):  
Bond Activation ◽  
Bond Formation ◽  
Ruthenium Catalyst

A Versatile Ruthenium Catalyst for CC Bond Formation by CH Bond Activation

2006 ◽  
Vol 118 (48) ◽  
pp. 8412-8415 ◽  
Author(s):  
Rémi Martinez ◽  
Reynald Chevalier ◽  
Sylvain Darses ◽  
Jean-Pierre Genet
Keyword(s):  
Bond Activation ◽  
Bond Formation ◽  
Ruthenium Catalyst

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.

Imine as a Linchpin Approach for Distal C(sp2)–H Functionalization

2020 ◽  
Author(s):  
Sukdev Bag ◽  
Sadhan Jana ◽  
Sukumar Pradhan ◽  
Suman Bhowmick ◽  
Nupur Goswami ◽  
...  
Keyword(s):  
Organic Molecules ◽  
Bond Activation ◽  
Bond Formation ◽  
Ancillary Ligand ◽  
Significant Challenge ◽  
Site Selectivity ◽  
Directing Group ◽  
Covalently Linked ◽  
Complex Organic ◽  
Post Functionalization

<p>Despite the widespread applications of C–H functionalization, controlling site selectivity remains a significant challenge. Covalently attached directing group (DG) served as an ancillary ligand to ensure proximal <i>ortho</i>-, distal <i>meta</i>- and <i>para</i>-C-H functionalization over the last two decades. These covalently linked DGs necessitate two extra steps for a single C–H functionalization: introduction of DG prior to C–H activation and removal of DG post-functionalization. We introduce here a transient directing group for distal C(<i>sp<sup>2</sup></i>)-H functionalization <i>via</i> reversible imine formation. By overruling facile proximal C-H bond activation by imine-<i>N</i> atom, a suitably designed pyrimidine-based transient directing group (TDG) successfully delivered selective distal C-C bond formation. Application of this transient directing group strategy for streamlining the synthesis of complex organic molecules without any necessary pre-functionalization at the distal position has been explored.</p>

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.

Peptide Modifications: Versatile Tools in Peptide and Natural Product Syntheses

Synlett ◽  
2019 ◽  
Vol 30 (11) ◽  
pp. 1289-1302 ◽  
Author(s):  
Phil Servatius ◽  
Lukas Junk ◽  
Uli Kazmaier
Keyword(s):  
Amino Acids ◽  
Natural Product ◽  
Bond Activation ◽  
Bond Formation ◽  
Side Chain ◽  
Peptide Backbone ◽  
Claisen Rearrangements ◽  
The Past ◽  
Allylic Alkylations ◽  
Peptide Modifications

Peptide modifications via C–C bond formation have emerged as valuable tools for the preparation and alteration of non-proteinogenic amino acids and the corresponding peptides. Modification of glycine subunits in peptides allows for the incorporation of unusual side chains, often in a highly stereoselective manner, orchestrated by the chiral peptide backbone. Moreover, modifications of peptides are not limited to the peptidic backbone. Many side-chain modifications, not only by variation of existing functional groups, but also by C–H functionalization, have been developed over the past decade. This account highlights the synthetic contributions made by our group and others to the field of peptide modifications and their application in natural product syntheses.1 Introduction2 Peptide Backbone Modifications via Peptide Enolates2.1 Chelate Enolate Claisen Rearrangements2.2 Allylic Alkylations2.3 Miscellaneous Modifications3 Side-Chain Modifications3.1 C–H Activation3.1.1 Functionalization via Csp3–H Bond Activation3.2.2 Functionalization via Csp2–H Bond Activation3.2 On Peptide Tryptophan Syntheses4 Conclusion

Recent Innovative Strategies for the Synthesis of Amines: From CN Bond Formation to CN Bond Activation

ChemSusChem ◽  
2009 ◽  
Vol 2 (8) ◽  
pp. 715-717 ◽  
Author(s):  
Karolin Krüger ◽  
Annegret Tillack ◽  
Matthias Beller
Keyword(s):  
Bond Activation ◽  
Bond Formation ◽  
Innovative Strategies

ChemInform Abstract: C-C Bond Formation via C-H Bond Activation under Protic Conditions: The Role of Phosphane Ligand and Cosolvent.

ChemInform ◽  
2010 ◽  
Vol 41 (18) ◽  
Author(s):  
Marc-Olivier Simon ◽  
Remi Martinez ◽  
Jean-Pierre Genet ◽  
Sylvain Darses
Keyword(s):  
Bond Activation ◽  
Bond Formation
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