Mild and Functional Group Tolerant Method for Tandem Palladium-Catalyzed Carbocyclization-Coupling of ε-Acetylenic β-Ketoesters with Aryl Bromides and Chlorides

2016 ◽  
Vol 358 (11) ◽  
pp. 1820-1825 ◽  
Author(s):  
Wojciech Chaładaj ◽  
Sylwester Domański
Keyword(s):  
Functional Group ◽  
Aryl Bromides ◽  
Palladium Catalyzed

Dual Nickel/Palladium-Catalyzed Reductive Cross-Coupling Reactions Between Two Phenol Derivatives

2020 ◽  
Author(s):  
Baojian Xiong ◽  
Yue Li ◽  
Yin Wei ◽  
Søren Kramer ◽  
Zhong Lian
Keyword(s):  
Functional Group ◽  
Low Cost ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Phenol Derivatives ◽  
Cross Coupling Reactions ◽  
Palladium Catalyzed ◽  
One Step ◽  
Aryl Tosylates ◽  
Low Sensitivity

Cross-coupling between substrates that can be easily derived from phenols is highly attractive due to the abundance and low cost of phenols. Here, we report a dual nickel/palladium-catalyzed reductive cross-coupling between aryl tosylates and aryl triflates; both substrates can be accessed in just one step from readily available phenols. The reaction has a broad functional group tolerance and substrate scope (>60 examples). Furthermore, it displays low sensitivity to steric effects demonstrated by the synthesis of a 2,2’disubstituted biaryl and a fully substituted aryl product. The widespread presence of phenols in natural products and pharmaceuticals allow for straightforward late-stage functionalization, illustrated with examples such as Ezetimibe and tyrosine. NMR spectroscopy and DFT calculations indicate that the nickel catalyst is responsible for activating the aryl triflate, while the palladium catalyst preferentially reacts with the aryl tosylate.

Enantioselective alpha-Arylation of Benzamides via Synergistic Nickel and Metallaphotoredox Catalysis

2019 ◽  
Author(s):  
John Montgomery ◽  
Alexander W. Rand
Keyword(s):  
Catalytic System ◽  
Functional Group ◽  
Enantiomeric Excess ◽  
New Method ◽  
Aryl Bromides

A new method to access alpha-arylated benzamides has been enabled by metallaphotoredox catalysis. This system allows for non-directed C–H functionalization of N-alkyl benzamides using a dual nickel/iridium catalytic system to form tertiary stereocenters in good enantiomeric excess and moderate yields. This reaction shows excellent functional group compatibility and can be performed using a number of sterically and electronically different aryl bromides and secondary benzamides.

Enantioselective alpha-Arylation of Benzamides via Synergistic Nickel and Metallaphotoredox Catalysis

2019 ◽  
Author(s):  
John Montgomery ◽  
Alexander W. Rand
Keyword(s):  
Catalytic System ◽  
Functional Group ◽  
Enantiomeric Excess ◽  
New Method ◽  
Aryl Bromides

A new method to access alpha-arylated benzamides has been enabled by metallaphotoredox catalysis. This system allows for non-directed C–H functionalization of N-alkyl benzamides using a dual nickel/iridium catalytic system to form tertiary stereocenters in good enantiomeric excess and moderate yields. This reaction shows excellent functional group compatibility and can be performed using a number of sterically and electronically different aryl bromides and secondary benzamides.

Solvent-free palladium-catalyzed C–O cross-coupling of aryl bromides with phenols

2021 ◽  
Vol 31 (3) ◽  
pp. 409-411
Author(s):  
Sergey A. Rzhevskiy ◽  
Maxim A. Topchiy ◽  
Vasilii N. Bogachev ◽  
Lidiya I. Minaeva ◽  
Ilia R. Cherkashchenko ◽  
...  
Keyword(s):  
Cross Coupling ◽  
Solvent Free ◽  
Aryl Bromides ◽  
Palladium Catalyzed
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