ChemInform Abstract: ASYMMETRIC NICKEL CATALYSIS IN THE CROSS-COUPLING REACTION OF ARYL HALIDES WITH GRIGNARD REAGENTS. A STUDY OF THE FACTORS INFLUENCING ASYMMETRIC INDUCTION

1983 ◽  
Vol 14 (51) ◽  
Author(s):  
G. CONSIGLIO ◽  
F. MORANDINI ◽  
O. PICCOLO
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Aryl Halides ◽  
Asymmetric Induction ◽  
Grignard Reagents ◽  
Nickel Catalysis ◽  
Factors Influencing ◽  
Cross Coupling Reaction ◽  
The Cross

scholarly journals Recent Progress in the Cross-Coupling Reaction Using Triorgano­silyl-Type Reagents

Synlett ◽  
2017 ◽  
Vol 28 (15) ◽  
pp. 1873-1884 ◽  
Author(s):  
Yasunori Minami ◽  
Tamejiro Hiyama ◽  
Takeshi Komiyama
Keyword(s):  
Recent Progress ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Aryl Halides ◽  
Organosilicon Compounds ◽  
Aryl Bromides ◽  
Cross Coupling Reaction ◽  
The Cross ◽  
Silicon Based ◽  
Coupling Polymerization

The silicon-based cross-coupling reaction has attracted much attention over recent decades because there are many advantages in using organosilicon compounds. However, the use of reagents with a triorganosilyl group as a key function remains to be established. This account summarizes our recent progress in cross-coupling chemistry with such silyl reagents.1 Introduction2 Preparation of HOMSi Reagents from Aryl Bromides and Disilanes3 HOMSi Reagents from Heteroaromatics and Hydrosilanes4 Cross-Coupling Polymerization with HOMSi Reagents5 Cross-Coupling with Aryl(triethyl)silanes6 Amination of Aryl Halides with N-TMS-Amines7 Conclusion and Perspective

Aldehydes and Ketones Influence Reactivity and Selectivity in Nickel-Catalyzed Suzuki-Miyaura Reactions

2019 ◽  
Author(s):  
Alasdair Cooper ◽  
David Leonard ◽  
Sonia Bajo ◽  
Paul Burton ◽  
David Nelson
Keyword(s):  
Carbonyl Group ◽  
Functional Groups ◽  
Oxidative Addition ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Aryl Halides ◽  
Cross Coupling Reaction ◽  
Site Selectivity ◽  
Aldehydes And Ketones ◽  
The Cross

We show that the energetically-favorable coordination of aldehydes and ketones – but not esters – to nickel(0) during Suzuki-Miyaura reactions can lead either to exquisite selectivity and enhanced reactivity, or to the inhibition<br>of the reaction. Aryl halides where the C-X bond is connected to the same π-system as an aldehyde or ketone functional<br>group undergo unexpectedly rapid oxidative addition, and are selectively cross-coupled during inter- and intramolecular<br>competition reactions. When aldehydes and ketones are present elsewhere, such as in the form of exogenous additives,<br>the cross-coupling reaction is inhibited depending on how strongly the pendant carbonyl group can coordinate to nickel(0). This work advances our understanding of how common functional groups interact with nickel(0) catalysts, and presents synthetic chemists with a tool that can be used to achieve site-selectivity in functionalized molecules. <br>

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