Metal-Catalyzed C(sp2)–N Bond Formation

2012 ◽  
pp. 55-85 ◽  
Author(s):  
Arkaitz Correa ◽  
Carsten Bolm
Keyword(s):  
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.

scholarly journals Transition Metal-Catalyzed α-Position Carbon–Carbon Bond Formations of Carbonyl Derivatives

Catalysts ◽  
2020 ◽  
Vol 10 (8) ◽  
pp. 861 ◽  
Author(s):  
Ha-Eun Lee ◽  
Dopil Kim ◽  
Ahrom You ◽  
Myung Hwan Park ◽  
Min Kim ◽  
...  
Keyword(s):  
Transition Metal ◽  
Carbonyl Compounds ◽  
Bond Formation ◽  
Chiral Ligand ◽  
Catalytic Systems ◽  
Carbon Bond ◽  
Carbonyl Derivatives ◽  
Carbon Carbon Bond ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed

α-Functionalization of carbonyl compounds in organic synthesis has traditionally been accomplished via classical enolate chemistry. As α-functionalized carbonyl moieties are ubiquitous in biologically and pharmaceutically valuable molecules, catalytic α-alkylations have been extensively studied, yielding a plethora of practical and efficient methodologies. Moreover, stereoselective carbon–carbon bond formation at the α-position of achiral carbonyl compounds has been achieved by using various transition metal–chiral ligand complexes. This review describes recent advances—in the last 20 years and especially focusing on the last 10 years—in transition metal-catalyzed α-alkylations of carbonyl compounds, such as aldehydes, ketones, imines, esters, and amides and in efficient carbon–carbon bond formations. Active catalytic species and ligand design are discussed, and mechanistic insights are presented. In addition, recently developed photo-redox catalytic systems for α-alkylations are described as a versatile synthetic tool for the synthesis of chiral carbonyl-bearing molecules.

Aryl—Aryl Bond Formation by Transition-Metal-Catalyzed Direct Arylation

ChemInform ◽  
2007 ◽  
Vol 38 (22) ◽  
Author(s):  
Dino Alberico ◽  
Mark E. Scott ◽  
Mark Lautens
Keyword(s):  
Transition Metal ◽  
Bond Formation ◽  
Direct Arylation ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed

ChemInform Abstract: New Access to H-Phosphonates via Metal-Catalyzed Phosphorus—Oxygen Bond Formation.

ChemInform ◽  
2008 ◽  
Vol 39 (1) ◽  
Author(s):  
Laetitia Coudray ◽  
Isabelle Abrunhosa-Thomas ◽  
Jean-Luc Montchamp
Keyword(s):  
Bond Formation ◽  
Metal Catalyzed ◽  
Oxygen Bond

ChemInform Abstract: A Sequential Metal-Catalyzed C-N Bond Formation in the Synthesis of 2-Amido-indoles.

ChemInform ◽  
2009 ◽  
Vol 40 (7) ◽  
Author(s):  
Pei-Yuan Yao ◽  
Yu Zhang ◽  
Richard P. Hsung ◽  
Kang Zhao
Keyword(s):  
Bond Formation ◽  
Metal Catalyzed

ChemInform Abstract: SYNTHESIS OF HETEROCYCLES BY CARBON-CARBON BOND FORMATION. I. NOBLE METAL-CATALYZED CYCLIZATION OF ACRYLIC ACID DIALLYL AMIDE

1976 ◽  
Vol 7 (27) ◽  
pp. no-no
Author(s):  
ERNST SCHMITZ ◽  
RAINER URBAN ◽  
UWE HUECK ◽  
GERHARD ZIMMERMANN ◽  
EGON GRUENDEMANN
Keyword(s):  
Acrylic Acid ◽  
Noble Metal ◽  
Bond Formation ◽  
Carbon Bond ◽  
Carbon Carbon Bond ◽  
Metal Catalyzed

Recent Developments in C–C Bond Formation Using Catalytic Reductive Coupling Strategies

Synthesis ◽  
2020 ◽  
Vol 52 (18) ◽  
pp. 2623-2638
Author(s):  
Joshua D. Sieber ◽  
Toolika Agrawal
Keyword(s):  
Bond Formation ◽  
Cross Coupling ◽  
Short Review ◽  
Reductive Coupling ◽  
Recent Developments ◽  
Molecular Complexity ◽  
Metal Catalyzed ◽  
Coupling Processes ◽  
Coupling Strategies

Metal-catalyzed reductive coupling processes have emerged as a powerful methodology for the introduction of molecular complexity from simple starting materials. These methods allow for an orthogonal approach to that of redox-neutral strategies for the formation of C–C bonds by enabling cross-coupling of starting materials not applicable to redox-neutral chemistry. This short review summarizes the most recent developments in the area of metal-catalyzed reductive coupling utilizing catalyst turnover by a stoichiometric reductant that becomes incorporated in the final product.1 Introduction2 Ni Catalysis3 Cu Catalysis4 Ru, Rh, and Ir Catalysis4.1 Alkenes4.2 1,3-Dienes4.3 Allenes4.4 Alkynes4.5 Enynes5 Fe, Co, and Mn Catalysis6 Conclusion and Outlook

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