Modular Synthesis of C2‐Symmetric Chiral TPyBPI Pincer Ligands and Application in Asymmetric Ni(II)‐Catalysed Friedel‐Crafts Alkylation DOI Open Access
Hong Cen, Liping Ding,

L.L. Liu

и другие.

Chinese Journal of Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Дек. 17, 2024

Comprehensive Summary Terpyridine ligands have been applied as a class of unique due to their rich coordination chemistry in the catalysis. Herein, we developed new C 2 ‐symmetric chiral terpyridine‐pyrroloimidazolone (TPy‐BPI). Their catalytic activity was evaluated asymmetric Friedel‐Crafts alkylation indoles with 2,3‐dioxopyrrolidines. Excellent yields (up 92%) and high enantioselectivities 97% ee) are obtained for wide range substrates under mild conditions. In addition 2,3‐dioxopyrrolidines, β , γ ‐unsaturated α ‐ketoesters were also compatible Ni(OTf) ‐TPy‐BPI ligand L1 ‐catalyzed reaction. Control experiments, single crystal structure two TPy‐BPI ‐Ni(OTf) complexes, DFT calculations revealed origins enantioselectivity. To best our knowledge, work is first report showing that terpyridine framework contained only nitrogen atoms coordinating metal, additional pyridine unit acted stereodirecting element, which different from previously reported containing all three metal.

Язык: Английский

Design of rigid chiral bipyridine-2NO tetradentate ligands: application in asymmetric catalysis DOI
Yuheng Wang, Pan Hu, Xirui Wang

и другие.

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(5), С. 1314 - 1321

Опубликована: Янв. 1, 2024

A new class of chiral bipyridine-2NO ligands, which incorporate the advantages both bipyridine skeleton and pyrroloimidazolone-based N -oxide moiety, was developed.

Язык: Английский

Процитировано

9

Bipyridine-N,N′-dioxides Catalysts: Design, Synthesis, and Application in Asymmetric Synthesis of 1H-Pyrazolo[3,4-b]pyridine Analogues DOI

Shijie Zhu,

Xue Tian, Jichang Liu

и другие.

Organic Letters, Год журнала: 2024, Номер 26(17), С. 3487 - 3492

Опубликована: Апрель 18, 2024

A novel type of highly efficient chiral C2-symmetric bipyridine-N,N′-dioxides ligand application in catalyzing Michael addition/Cyclization 5-aminopyrazoles with α,β-unsaturated 2-acyl imidazoles has been developed, affording the corresponding adducts 85–97% yield up to 99% enantioselectivity under mild conditions a lower catalyst loading and broad scope. Remarkably, this protocol exhibits advantages terms reactivity enantioselectivity, giving fact that as low 2.2 mol % L1 2.0 Ni(OTf)2 can promote title reaction on gram scale afford desired product excellent enantioselectivity.

Язык: Английский

Процитировано

7

Py-2NO ligand enabled Ni(ii)-catalyzed asymmetric Michael addition reaction of indoles with β,γ-unsaturated α-keto esters DOI

Zi‐Yue Chen,

Xirui Wang,

Ke‐Lan Xu

и другие.

New Journal of Chemistry, Год журнала: 2024, Номер 48(4), С. 1688 - 1695

Опубликована: Янв. 1, 2024

This work diversified the Py-2NO ligand library recently developed by our group and further expanded application of chiral ligands in asymmetric catalysis.

Язык: Английский

Процитировано

6

Chiral Phenol‐2NO Ligand Cooperation with Achiral Organic Base in the Zn(II)‐Catalyzed Asymmetric Alkylation Reaction of Indoles DOI

Ke‐Lan Xu,

Yuheng Wang, Xirui Wang

и другие.

Chinese Journal of Chemistry, Год журнала: 2024, Номер 42(13), С. 1474 - 1480

Опубликована: Март 1, 2024

Comprehensive Summary The privileged C 2 ‐symmetric rigid phenol‐type ligand is more attractive but challenging in asymmetric catalysis. Herein, we designed and synthesized a class of rigid‐featured chiral tridentate Phenol‐2NO ligands, that incorporate the advantages both phenol skeleton pyrroloimidazolone‐based N ‐oxide moiety, from readily available L ‐prolinamides operationally simple two steps up to 44% overall yield. More importantly, using an achiral quinoline derivative as additive, newly developed could serve anioic upon deprotonative activation coordinate Zn(II) form highly enantioselective catalyst for Michael‐type Friedel‐Crafts alkylation reaction indoles with 2,3‐dioxopyrrolidines. Excellent yields (up 90%) high enantioselectivities 99% ee) are obtained wide range substrates under mild conditions. Experiments DFT calculations revealed mechanism origins enantioselectivity. This also represented first ligand/metal complex by organic base additive

Язык: Английский

Процитировано

6

Phen-2NO, a new C2-symmetric rigid-featured tetradentate ligand, and its application in the asymmetric alkylation reaction of indoles DOI

Zi‐Yue Chen,

Ke‐Lan Xu,

Xirui Wang

и другие.

New Journal of Chemistry, Год журнала: 2024, Номер 48(15), С. 6670 - 6675

Опубликована: Янв. 1, 2024

A new class of C 2 -symmetric rigid-featured chiral phen ligands that provide the N , O -tetradentate coordination moiety and two additional -dioxides were rationally designed developed.

Язык: Английский

Процитировано

3

Naphthyridine–2NO, a new C2-symmetric rigid tetradentate bimetallic ligand and its application in asymmetric Friedel–Crafts alkylation DOI
Pan Hu,

Ke‐Lan Xu,

Xirui Wang

и другие.

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(9), С. 2600 - 2606

Опубликована: Янв. 1, 2024

The development of a series novel and easily accessed chiral naphthyridine-type binucleating ligands for asymmetric catalysis.

Язык: Английский

Процитировано

3

Modular Synthesis of C2‐Symmetric Chiral TPyBPI Pincer Ligands and Application in Asymmetric Ni(II)‐Catalysed Friedel‐Crafts Alkylation DOI Open Access
Hong Cen, Liping Ding,

L.L. Liu

и другие.

Chinese Journal of Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Дек. 17, 2024

Comprehensive Summary Terpyridine ligands have been applied as a class of unique due to their rich coordination chemistry in the catalysis. Herein, we developed new C 2 ‐symmetric chiral terpyridine‐pyrroloimidazolone (TPy‐BPI). Their catalytic activity was evaluated asymmetric Friedel‐Crafts alkylation indoles with 2,3‐dioxopyrrolidines. Excellent yields (up 92%) and high enantioselectivities 97% ee) are obtained for wide range substrates under mild conditions. In addition 2,3‐dioxopyrrolidines, β , γ ‐unsaturated α ‐ketoesters were also compatible Ni(OTf) ‐TPy‐BPI ligand L1 ‐catalyzed reaction. Control experiments, single crystal structure two TPy‐BPI ‐Ni(OTf) complexes, DFT calculations revealed origins enantioselectivity. To best our knowledge, work is first report showing that terpyridine framework contained only nitrogen atoms coordinating metal, additional pyridine unit acted stereodirecting element, which different from previously reported containing all three metal.

Язык: Английский

Процитировано

0