scholarly journals Cross C–S coupling reaction catalyzed by copper(i) N-heterocyclic carbene complexes

RSC Advances ◽  
2017 ◽  
Vol 7 (9) ◽  
pp. 4912-4920 ◽  
Author(s):  
Wei-Kai Huang ◽  
Wei-Ting Chen ◽  
I.-Jui Hsu ◽  
Chien-Chung Han ◽  
Shin-Guang Shyu
Keyword(s):  
Dft Calculation ◽  
Coupling Reaction ◽  
Heterocyclic Carbenes ◽  
Aryl Halides ◽  
Catalytic Cycle ◽  
Carbene Complexes ◽  
The Cross

Copper(i) N-heterocyclic carbenes catalyze the cross C–S coupling reaction with good activities towards aryl halides. A plausible catalytic cycle is proposed, with the support of DFT calculation.

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>

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>

Piperazine as an Inexpensive and Efficient Ligand for Pd-Catalyzed Homocoupling Reactions to Synthesize Bipyridines and Their Analogues

2019 ◽  
Vol 16 (1) ◽  
pp. 173-180
Author(s):  
Mingwei Chen ◽  
Jinyu Hu ◽  
Xiaoli Tang ◽  
Qiming Zhu
Keyword(s):  
Transition Metal ◽  
Oxidation State ◽  
Coupling Reaction ◽  
Aryl Halides ◽  
Metal Species ◽  
Good Substrate ◽  
Active Metal ◽  
Homocoupling Reaction ◽  
Catalytic Cycles ◽  
Reductive Homocoupling

Aim and Objective: The synthesis of bipyridines, especially 2, 2’-bipyridines, remains challenging because the catalytic cycle can be inhibited due to coordination of bipyridine to transition metal. Thus, the development of efficient methods for the synthesis of bipyridines is highly desirable. In the present work, we presented a promising approach for preparation of bipyridines via a Pd-catalyzed reductive homocoupling reaction with simple piperazine as a ligand. Materials and Methods: Simple and inexpensive piperazine was used as a ligand for Pd-catalyzed homocoupling reaction. The combination of Pd(OAc)2 and piperazine in dimethylformamide (DMF) was observed to form an excellent catalyst and efficiently catalyzed the homocoupling of azaarenyl halides, in which DMF was used as the solvent without excess reductants although stoichiometric reductant was generally required to generate the low-oxidation-state active metal species in the catalytic cycles. </P><P> Results: In this case, good to excellent yields of bipyridines and their (hetero) aromatic analogues were obtained in the presence of 2.5 mol% of Pd(OAc)2 and 5 mol% of piperazine, using K3PO4 as a base in DMF at 140°C. Conclusion: According to the results, piperazine as an inexpensive and efficient ligand was used in the Pd(OAc)2-catalyzed homocoupling reaction of heteroaryl and aryl halides. The coupling reaction was operationally simple and displayed good substrate compatibility.

Nickel-Catalyzed Multicomponent Coupling Reaction of Alkyl Halides, Isocyanides and H2O: An Expedient Way to Access Alkyl Amides

Synthesis ◽  
2020 ◽  
Vol 52 (22) ◽  
pp. 3466-3472
Author(s):  
Yunkui Liu ◽  
Bingwei Zhou ◽  
Qiao Li ◽  
Hongwei Jin
Keyword(s):  
Functional Group ◽  
Coupling Reaction ◽  
Alkyl Halides ◽  
Previous Literature ◽  
Catalytic Cycle ◽  
Reaction Conditions ◽  
Multicomponent Coupling ◽  
Easy Operation

We herein describe a Ni-catalyzed multicomponent coupling reaction of alkyl halides, isocyanides, and H2O to access alkyl amides. Bench-stable NiCl2(dppp) is competent to initiate this transformation under mild reaction conditions, thus allowing easy operation and adding practical value. Substrate scope studies revealed a broad functional group tolerance and generality of primary and secondary alkyl halides in this protocol. A plausible catalytic cycle via a SET process is proposed based on preliminary experiments and previous literature.

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