Copper(I)-Catalyzed Reductive Cross-Coupling ofN-Tosylhydrazones with Amides: A Straightforward Method for the Construction of C(sp3)N Amide Bonds from Aldehydes

2015 ◽  
Vol 357 (16-17) ◽  
pp. 3441-3446 ◽  
Author(s):  
Peng Xu ◽  
Fu-She Han ◽  
Yan-Hua Wang
Keyword(s):  
Cross Coupling ◽  
Amide Bonds ◽  
Straightforward Method

Protocol for Palladium/N-Heterocyclic Carbene-Catalyzed Suzuki–Miyaura Cross-Coupling of Amides by N–C(O) Activation

Synthesis ◽  
2020 ◽  
Author(s):  
Peng Lei ◽  
Guangchen Li ◽  
Michal Szostak ◽  
Yun Ling ◽  
Jie An ◽  
...  
Keyword(s):  
Organic Chemistry ◽  
Room Temperature ◽  
Bond Activation ◽  
Process Development ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Amide Bonds ◽  
Cross Coupling Reactions ◽  
Synthetic Procedure ◽  
Operational Simplicity

AbstractAmides are among the most important and ubiquitous functional groups in organic chemistry and process development. In this Practical Synthetic Procedure, a protocol for the Suzuki–Miyaura cross-coupling of amides by selective N–C(O) bond activation catalyzed by commercially available, air- and moisture-stable palladium/N-heterocyclic carbene (NHC) complexes is described. The procedure described involves [Pd(IPr)(cin)Cl] [IPr = 2,6-(diisopropylphenyl)imidazol-2-ylidene, cin = cinnamyl] at 0.10 mol% at room temperature and is performed on decagram scale. Furthermore, a procedure for the synthesis of amide starting materials is accomplished via selective N-tert-butoxycarbonylation, which is the preferred method over N-acylation. The present protocol carries advantages of operational simplicity, commercial availability of catalysts, and excellent conversions at low catalyst loadings. The method is generally useful for activation of N–C(O) amide bonds in a broad spectrum of amide precursors. The protocol should facilitate the implementation of amide cross-coupling reactions.

Metal-free synthesis of 2,2-disubstituted indolin-3-ones

2019 ◽  
Vol 17 (8) ◽  
pp. 2199-2203 ◽  
Author(s):  
Xinpeng Jiang ◽  
Bingbin Zhu ◽  
Kai Lin ◽  
Guan Wang ◽  
Wei-Ke Su ◽  
...  
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Metal Catalyst ◽  
Facile Synthesis ◽  
Metal Free ◽  
Cross Coupling Reaction ◽  
Straightforward Method

A straightforward method for the synthesis of indolin-3-ones bearing a C2-quaternary functionality is reported. This cross-coupling reaction allows the facile synthesis of a series of 2,2-disubstituted indolin-3-ones in the absence of a metal catalyst in up to 94% yields.

Methyl Esters as Cross-Coupling Electrophiles: Direct Synthesis of Amide Bonds

ACS Catalysis ◽  
2019 ◽  
Vol 9 (5) ◽  
pp. 4426-4433 ◽  
Author(s):  
Yan-Long Zheng ◽  
Stephen G. Newman
Keyword(s):  
Methyl Esters ◽  
Direct Synthesis ◽  
Cross Coupling ◽  
Amide Bonds

Photoredox/Pd dual-catalytic three-component cross-coupling

2020 ◽  
Author(s):  
Logan Forshee ◽  
Kaitie Cartwright ◽  
Jon Tunge ◽  
Megan Hegarty
Keyword(s):  
Cross Coupling
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