Gold-catalyzed para-selective C–H bond alkylation of benzene derivatives with donor/acceptor-substituted diazo compounds

2017 ◽  
Vol 53 (73) ◽  
pp. 10164-10167 ◽  
Author(s):  
Ben Ma ◽  
Jiaojiao Wu ◽  
Lu Liu ◽  
Junliang Zhang
Keyword(s):  
Diazo Compounds ◽  
Benzene Derivatives ◽  
Alkylation Of Benzene ◽  
Donor Acceptor

A gold(i)-catalyzed cascade C–H functionalization of unactivated arenes with α-aryl α-diazoesters with electron-withdrawing groups has been developed.

Highlypara-Selective C−H Alkylation of Benzene Derivatives with 2,2,2-Trifluoroethyl α-Aryl-α-Diazoesters

2017 ◽  
Vol 56 (10) ◽  
pp. 2749-2753 ◽  
Author(s):  
Ben Ma ◽  
Zhaowei Chu ◽  
Ben Huang ◽  
Zhenli Liu ◽  
Lu Liu ◽  
...  
Keyword(s):  
Benzene Derivatives ◽  
Alkylation Of Benzene

Highly para-selective C‒H alkylation of unactivated arenes with α-aryl-α-diazoesters catalyzed by gold(I) immobilized on MCM-41

2019 ◽  
Vol 44 (3-4) ◽  
pp. 174-180 ◽  
Author(s):  
Yingying Du ◽  
Fang Yao ◽  
Mingzhong Cai
Keyword(s):  
Recyclable Catalyst ◽  
Benzene Derivatives ◽  
Mild Conditions ◽  
Alkylation Of Benzene ◽  
Mcm 41 ◽  
Electron Withdrawing Substituents

The heterogeneous gold(I)-catalyzed highly para-selective C(sp2)–H bond alkylation of benzene derivatives with α-aryl-α-diazoesters possessing electron-withdrawing substituents on the aryl rings are achieved. The reactions proceed under mild conditions in good to excellent yields by using an MCM-41-anchored diphenylphosphine gold(I) complex [MCM-41-PPh2-AuOTf] as a recyclable catalyst.

scholarly journals Effects of Axial Solvent Coordination to Dirhodium Complexes on Reactivity and Selectivity in C–H Insertion Reactions: A Computational Study

2021 ◽  
Author(s):  
Croix Laconsay ◽  
Anna Pla-Quintana ◽  
Dean Tantillo
Keyword(s):  
Density Functional ◽  
Computational Study ◽  
Density Functional Theory Calculations ◽  
Diazo Compounds ◽  
Insertion Reactions ◽  
Functional Theory ◽  
Axial Ligation ◽  
Donor Acceptor ◽  
Solvent Molecules ◽  
Dirhodium Complexes

Density functional theory calculations were used to systematically explore the effects of axial ligation by solvent molecules on the reactivity and selectivity of dirhodium tetracarboxylates with diazo compounds in the context of C–H insertion into propane. Insertions on three types of diazo compounds—acceptor/acceptor, donor/acceptor, and donor/donor—promoted by dirhodium tetraformate were tested with and without axial solvent ligation for no surrounding solvent, dichloromethane, isopropanol, and acetonitrile. Magnitudes, origins, and consequences of structural and electronic changes arising from axial ligation were characterized. The results suggest that axial ligation affects barriers for N2 extrusion and C–H insertion, the former to a larger extent.

scholarly journals Effects of Axial Solvent Coordination to Dirhodium Complexes on Reactivity and Selectivity in C–H Insertion Reactions: A Computational Study

2021 ◽  
Author(s):  
Croix Laconsay ◽  
Anna Pla-Quintana ◽  
Dean Tantillo
Keyword(s):  
Density Functional ◽  
Computational Study ◽  
Density Functional Theory Calculations ◽  
Diazo Compounds ◽  
Insertion Reactions ◽  
Functional Theory ◽  
Axial Ligation ◽  
Donor Acceptor ◽  
Solvent Molecules ◽  
Dirhodium Complexes

Density functional theory calculations were used to systematically explore the effects of axial ligation by solvent molecules on the reactivity and selectivity of dirhodium tetracarboxylates with diazo compounds in the context of C–H insertion into propane. Insertions on three types of diazo compounds—acceptor/acceptor, donor/acceptor, and donor/donor—promoted by dirhodium tetraformate were tested with and without axial solvent ligation for no surrounding solvent, dichloromethane, isopropanol, and acetonitrile. Magnitudes, origins, and consequences of structural and electronic changes arising from axial ligation were characterized. The results suggest that axial ligation affects barriers for N2 extrusion and C–H insertion, the former to a larger extent.

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