Cobalt‐Catalyzed Hydroarylation of 2,3‐Dihydrofuran to Access α‐Arylated Tetrahydrofurans DOI

Hao-Kai Sun,

Xi Lu, Yao Fu

et al.

ChemCatChem, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 11, 2024

Abstract The α ‐arylated tetrahydrofurans, commonly found in biologically active molecules, exhibit diverse biological activities and pharmacological effects. functionalization of 2,3‐dihydrofuran offers a potential route for the synthesis substituted tetrahydrofurans. Nevertheless, development earth‐abundant metal‐catalyzed regioselective hydrofunctionalization tetrahydrofurans remains to be pursued. Herein, we report cobalt‐catalyzed hydroarylation 2,3‐dihydrofuran, which serves as first example cobalt hydride‐catalyzed alkene hydroarylation. This reaction provides an efficient method with high efficiency, exclusive ‐arylation selectivity, remarkable functional group compatibility.

Language: Английский

IronIII-catalyzed asymmetric inverse-electron-demand hetero-Diels–Alder reaction of dioxopyrrolidines with simple olefins DOI Creative Commons

Tangyu Zhan,

Liang Zhou, Yuqiao Zhou

et al.

Chemical Science, Journal Year: 2024, Volume and Issue: 15(13), P. 4797 - 4803

Published: Jan. 1, 2024

A highly enantioselective [4 + 2] cycloaddition of a number simple olefins with cyclic hetero-diene dioxopyrrolidines is realized by chiral iron( iii )/ N , ′-dioxide complex catalyst.

Language: Английский

Citations

11
Quinone-Initiated Photocatalytic Enantioselective Giese Radical Addition with Ethers, Thioethers, Amines, and Alkanes DOI
Yao Luo, Yuqiao Zhou,

Fengnan Xiao

et al.

ACS Catalysis, Journal Year: 2024, Volume and Issue: 14(16), P. 12031 - 12041

Published: July 29, 2024

Photocatalytic enantioselective Giese radical addition with inert C(sp3)–H bonds represents a highly efficient and economically favorable approach to synthesizing diverse value-added chiral molecules from abundant feedstock. Herein, we disclose quinone-initiated photocatalytic asymmetric of α-substituted acrylamides by applying simple quinones as HAT photocatalysts in combination N,N′-dioxide/praseodymium(III) catalyst. A wide array ethers, thioethers, selenide, amines, alkanes can smoothly transform into the corresponding α-aryl amide derivatives satisfactory enantioselectivities (68 examples, up 95% ee) under mild conditions. Based on spectroscopy studies control experiments, catalytic cycle was proposed, DFT calculations revealed that interaction between quinone Lewis acid essential for enantio-induction back hydrogen atom transfer process.

Language: Английский

Citations

8
Copper Catalyzed [3+2] Annulation Reaction of Exocyclic Sulfonyl Enamides for the Synthesis of N,O‐Spiroketal and Spiroketal DOI

Wen‐Fu Cheng,

Shan‐Zeng Gao,

Yuchen Yang

et al.

Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: 30(44)

Published: June 1, 2024

A copper-catalyzed [3+2] annulation reaction of exocyclic enamines/enol ethers with 1,4-benzoquinone esters has been developed, providing facile access to N,O-spiroketals and spiroketals under mild conditions broad substrate scope (26 examples, 71-94 % yields). Gram scale synthesis chemical transformations demonstrated that this method is potentially useful in the natural products drugs containing a N,O- spiroketal moiety. The chiral N,O-spiroketal could be obtained 98 ee after recrystallization, when SaBOX ligand was employed.

Language: Английский

Citations

2
Asymmetric dearomatization of benzyl 1-naphthyl ethers via [1,3] O-to-C rearrangement DOI

Hongkun Zeng,

Gang Wen, Lili Lin

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(58), P. 7507 - 7510

Published: Jan. 1, 2024

An asymmetric dearomatization reaction of benzyl 1-naphthyl ethers accelerated by a chiral N , ′-dioxide/Co( ii ) complex is disclosed. Experiment results indicated that the proceeds via tight ion-pair intermediate.

Language: Английский

Citations

1
Ir/Brønsted acid dual-catalyzed asymmetric synthesis of bisbenzannulated spiroketals and spiroaminals from isochroman ketals DOI
Yang Chen, Hui Yan, Hanliang Zheng

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(20), P. 5831 - 5840

Published: Jan. 1, 2024

An Ir/Brønsted acid dual-catalyzed asymmetric cascade reaction of 2-(1-hydroxyallyl)phenols with isochroman ketals was developed, affording antifungal spiroketals high enantioselectivities.

Language: Английский

Citations

1
Asymmetric catalytic concise synthesis of 3-(3-indolomethyl)-oxindoles for the construction of trigolute analogs DOI

Zun Yang,

Zheng Jiang, Zheng Tan

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(78), P. 10926 - 10929

Published: Jan. 1, 2024

In this paper, a newly asymmetric catalytic construction of 3-(3-indolomethyl)oxindoles was developed. Taking use method as the key step, concise syntheses trigolute analogs accomplished.

Language: Английский

Citations

1
Brønsted acid catalyzed [4 + 2] cycloaddition for the synthesis of bisbenzannulated spiroketals with antifungal activities DOI

Teng Hu,

Yuxuan Zhao,

Xiaoyan Luo

et al.

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(23), P. 4656 - 4661

Published: Jan. 1, 2024

The intermolecular [4 + 2] cycloaddition of

Language: Английский

Citations

0
De novo synthesis of atropisomeric benzofurans via Cu/SPDO complex catalyzed asymmetric formal [3 + 2] annulation DOI

Fan‐Xiao Meng,

Xingyu Wang,

Ka Lu

et al.

Science China Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Sept. 9, 2024

Language: Английский

Citations

0
Cobalt‐Catalyzed Hydroarylation of 2,3‐Dihydrofuran to Access α‐Arylated Tetrahydrofurans DOI

Hao-Kai Sun,

Xi Lu, Yao Fu

et al.

ChemCatChem, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 11, 2024

Abstract The α ‐arylated tetrahydrofurans, commonly found in biologically active molecules, exhibit diverse biological activities and pharmacological effects. functionalization of 2,3‐dihydrofuran offers a potential route for the synthesis substituted tetrahydrofurans. Nevertheless, development earth‐abundant metal‐catalyzed regioselective hydrofunctionalization tetrahydrofurans remains to be pursued. Herein, we report cobalt‐catalyzed hydroarylation 2,3‐dihydrofuran, which serves as first example cobalt hydride‐catalyzed alkene hydroarylation. This reaction provides an efficient method with high efficiency, exclusive ‐arylation selectivity, remarkable functional group compatibility.

Language: Английский

Citations

0