Cross-coupling reactions with esters, aldehydes, and alcohols

2021 ◽  
Author(s):  
Yan-Long Zheng ◽  
Stephen G. Newman
Keyword(s):  
Functional Groups ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Feature Article ◽  
Cross Coupling Reactions

This feature article describes how diverse oxygen-containing functional groups such as esters, aldehydes, and alcohols can participate in cross-coupling reactions to prepare amides, ketones, alcohols, and beyond.

Carbon-Heteroatom Cross-Coupling via an Electronically Excited Nickel (II) Complex

2019 ◽  
Author(s):  
Randolph Escobar ◽  
Jeffrey Johannes
Keyword(s):  
Energy Transfer ◽  
Functional Groups ◽  
Cross Coupling ◽  
Reductive Elimination ◽  
Aryl Halides ◽  
Coupling Reactions ◽  
General Methodology ◽  
Cross Coupling Reactions ◽  
Electronically Excited ◽  
Energy Transfer Pathway

<div>While carbon-heteroatom cross coupling reactions have been extensively studied, many methods are specific and</div><div>limited to a set of substrates or functional groups. Reported here is a method that allows for C-O, C-N and C-S cross coupling reactions under one general methodology. We propose that an energy transfer pathway, in which an iridium photosensitizer produces an excited nickel (II) complex, is responsible for the key reductive elimination step that couples aryl halides to 1° and 2° alcohols, anilines, thiophenols, carbamates and sulfonamides.</div>

scholarly journals Photoredox-catalyzed stereoselective alkylation of enamides with N-hydroxyphthalimide esters via decarboxylative cross-coupling reactions

2019 ◽  
Vol 10 (38) ◽  
pp. 8792-8798 ◽  
Author(s):  
Jing-Yu Guo ◽  
Ze-Yu Zhang ◽  
Ting Guan ◽  
Lei-Wen Mao ◽  
Qian Ban ◽  
...  
Keyword(s):  
Functional Groups ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Cross Coupling Reactions

Stereoselective β-C(sp2)–H alkylation of enamides with N-hydroxyphthalimide esters is demonstrated, affording geometrically defined alkylated enamides bearing various functional groups.

Pd/Cu-free Magnetic Cobalt Catalyst for C-N cross Coupling Reactions: Synthesis of Abemaciclib and Fedratinib

2021 ◽  
Author(s):  
Zahra Khorsandi ◽  
Abdol R. Hajipour ◽  
Mohammad R. Sarfjoua ◽  
Rajender S Varma
Keyword(s):  
Magnetic Nanoparticles ◽  
Functional Groups ◽  
Cobalt Catalyst ◽  
Cross Coupling ◽  
Catalyst System ◽  
Coupling Reactions ◽  
Cross Coupling Reactions ◽  
Nano Catalyst ◽  
Natural Ligands ◽  
Cobalt Species

Herein, the synthesis of a nano-catalyst system comprising magnetic nanoparticles as core and edible natural ligands bearings functional groups for supporting the cobalt species was accomplished. Subsequent to characterization, its...

scholarly journals Carbon-Heteroatom Cross-Coupling via an Electronically Excited Nickel (II) Complex

2019 ◽  
Author(s):  
Randolph Escobar ◽  
Jeffrey Johannes
Keyword(s):  
Energy Transfer ◽  
Functional Groups ◽  
Cross Coupling ◽  
Reductive Elimination ◽  
Aryl Halides ◽  
Coupling Reactions ◽  
General Methodology ◽  
Cross Coupling Reactions ◽  
Electronically Excited ◽  
Energy Transfer Pathway

<div>While carbon-heteroatom cross coupling reactions have been extensively studied, many methods are specific and</div><div>limited to a set of substrates or functional groups. Reported here is a method that allows for C-O, C-N and C-S cross coupling reactions under one general methodology. We propose that an energy transfer pathway, in which an iridium photosensitizer produces an excited nickel (II) complex, is responsible for the key reductive elimination step that couples aryl halides to 1° and 2° alcohols, anilines, thiophenols, carbamates and sulfonamides.</div>

scholarly journals Nickel versus Palladium in Cross-Coupling Catalysis: On the Role of Substrate Coordination to Zerovalent Metal Complexes

Synthesis ◽  
2019 ◽  
Vol 52 (04) ◽  
pp. 565-573 ◽  
Author(s):  
Alasdair K. Cooper ◽  
Paul M. Burton ◽  
David J. Nelson
Keyword(s):  
Functional Groups ◽  
Density Functional ◽  
Aryl Halide ◽  
Cross Coupling ◽  
Density Functional Theory Calculations ◽  
Detailed Comparison ◽  
Coupling Reactions ◽  
Functional Theory ◽  
Cross Coupling Reactions

A detailed comparison of the effect of coordinating functional groups on the performance of Suzuki–Miyaura reactions catalysed by nickel and palladium is reported, using competition experiments, robustness screening, and density functional theory calculations. Nickel can interact with a variety of functional groups, which manifests as selectivity in competitive cross-coupling reactions. The presence of these functional groups on exogenous additives has effects on cross-coupling reactions that range from a slight improvement in yield to the complete cessation of the reaction. In contrast, palladium does not interact sufficiently strongly with these functional groups to induce selectivity in cross-coupling reactions; the selectivity of palladium-catalysed cross-coupling reactions is predominantly governed by aryl halide electronic properties.

Oxidant-free oxidative gold catalysis: the new paradigm in cross-coupling reactions

2018 ◽  
Vol 54 (79) ◽  
pp. 11069-11083 ◽  
Author(s):  
Manjur O. Akram ◽  
Somsuvra Banerjee ◽  
Sagar S. Saswade ◽  
Vaibhav Bedi ◽  
Nitin T. Patil
Keyword(s):  
Cross Coupling ◽  
Gold Catalysis ◽  
Coupling Reactions ◽  
New Paradigm ◽  
Feature Article ◽  
The Core ◽  
Cross Coupling Reactions ◽  
Research Activities ◽  
Promising Area

The construction of C–C and C–X (X = hetero atom) bonds is the core aspect for the assembly of molecules. This feature article critically presents an overview of all the redox neutral cross-coupling reactions enabled by gold catalysis, which we believe would stimulate further research activities in this promising area.

4 Electroreductive Reactions

2022 ◽  
Author(s):  
P. Schiltz ◽  
C. Gosmini
Keyword(s):  
Carbon Dioxide ◽  
Oxygen Reduction ◽  
Functional Groups ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Reduction Reactions ◽  
Oxygen Reduction Reactions ◽  
Cross Coupling Reactions

This review covers a variety of electroreductive reactions. A range of catalyzed electroreductive cross-coupling reactions, electroreduction of various functional groups and carbon dioxide, decarboxylation reactions, and oxygen reduction reactions are discussed.

scholarly journals POxAP Precatalysts and the Negishi Cross-Coupling Reaction

Synthesis ◽  
2019 ◽  
Vol 52 (01) ◽  
pp. 51-59
Author(s):  
Shuang-Qi Tang ◽  
Martine Schmitt ◽  
Frédéric Bihel
Keyword(s):  
Functional Groups ◽  
Oxidative Addition ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Catalytic Activities ◽  
Cross Coupling Reactions ◽  
Cross Coupling Reaction ◽  
Wide Range ◽  
Organozinc Reagents

Recently developed for the Fukuyama reaction, post-oxidative addition precatalysts (POxAPs) are also very efficient in catalyzing Negishi cross-coupling reactions between organohalides and organozinc reagents. Using very low catalyst loadings, POxAPs show similar catalytic activities to those of classical precatalysts such as XPhos Pd G4 or PEPPSI-IPr, with turnover numbers of up to 93,000. POxAPs are easily prepared, are stable to air and moisture, tolerate a wide range of functional groups in the Negishi cross-coupling reaction and contribute advantageously to the arsenal of organic chemists in terms of Pd precatalysts.

scholarly journals A novel 4-aminoantipyrine-Pd(II) complex catalyzes Suzuki–Miyaura cross-coupling reactions of aryl halides

2014 ◽  
Vol 10 ◽  
pp. 2821-2826 ◽  
Author(s):  
Claudia Araceli Contreras-Celedón ◽  
Darío Mendoza-Rayo ◽  
José A Rincón-Medina ◽  
Luis Chacón-García
Keyword(s):  
Functional Groups ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Aryl Halides ◽  
Coupling Reactions ◽  
Reaction Conditions ◽  
Cross Coupling Reactions ◽  
Highly Active ◽  
Cross Coupling Reaction ◽  
Phenylboronic Acids

A simple and efficient catalytic system based on a Pd complex of 4-aminoantipyrine, 4-AAP–Pd(II), was found to be highly active for Suzuki–Miyaura cross-coupling of aryl iodides and bromides with phenylboronic acids under mild reaction conditions. Good to excellent product yields from the cross-coupling reaction can be achieved when the reaction is carried out in ethanol, in the open air, using low loading of 4-AAP–Pd(II) as a precatalyst, and in the presence of aqueous K2CO3 as the base. A variety of functional groups are tolerated.

Exploiting the dual role of ethynylbenziodoxolones in gold-catalyzed C(sp)–C(sp) cross-coupling reactions

2017 ◽  
Vol 53 (56) ◽  
pp. 7937-7940 ◽  
Author(s):  
Somsuvra Banerjee ◽  
Nitin T. Patil
Keyword(s):  
Functional Groups ◽  
Catalytic System ◽  
Cross Coupling ◽  
Dual Role ◽  
Coupling Reactions ◽  
Terminal Alkynes ◽  
Cross Coupling Reactions ◽  
Polar Functional Groups ◽  
Transfer Agents

Reported herein is the gold-catalyzed alkynylation of terminal alkynes using ethynylbenziodoxolones (EBXs), where EBXs serve a dual role as oxidants as well as alkyne transfer agents to access unsymmetrical 1,3-diynes. Hence, the catalytic system requires no external oxidants and is compatible with a broad range of substrates, including those with polar functional groups such as NH, OH and B(OH)2.

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