Guo‐Ping Ge

Ningbo University

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Recent progress in the radical α-C(sp³)–H functionalization of ketones

Organic & Biomolecular Chemistry (2021)

Jiao‐Zhe Li Weikang Zhang Guo‐Ping Ge Hong Zheng Wen‐Ting Wei

The direct use structurally simple ketones as α-ketone radical sources for α-C(sp3)-H functionalization is a sustainable and powerful approach for constructing complex and multifunctional chemical scaffolds with diverse applications. The reactions of α-ketone radicals with alkenes, alkynes, enynes, imides, and imidazo[1,2-a]pyridines have broadened the structural diversity and complexity of ketones. Through chosen illustrative examples, we outline the recent progress in the development of methods that enable the radical α-C(sp3)-H functionalization of ketones, with an emphasis on radical initiation systems and possible mechanisms of the transformations. The application of these strategies is illustrated by the synthesis of several biologically active molecules and drug molecules. Further subdivision is based on substrate type and reaction type.

Surface Modification

10.1039/d1ob01408k

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Citations (18)

Room Temperature, Metal-Free, Radical Chloroazidation of 1,6-Enynes

Synlett (2018)

Wen‐Ting Wei Wei‐Wei Ying Wei‐Ting Chen Wenhui Bao Le‐Han Gao

Without employing any transition metal, a mild, practical, and environmentally attractive methodology has been developed for the chloroazidation of 1,6-enynes at room temperature. In this radical cascade process, three new chemical bonds, including C–Cl (Br, I), C–N, and C–C bonds, are formed in one step for the construction of 2-pyrrolidinones. The method is valuable because of its mild reaction conditions, operational simplicity, and the rich biological activity of the corresponding 2-pyrrolidinone products.

Pyrrolidinones

Reaction conditions

Simplicity

10.1055/s-0037-1609752

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Citations (12)

CCDC 896535: Experimental Crystal Structure Determination

The Cambridge Structural Database (2012)

Guo‐Ping Ge Chunyan Li

An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.

10.5517/ccz2xhf

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Chemodivergent Tandem Radical Cyclization of Alkene‐Substituted Quinazolinones: Rapid Access to Mono‐ and Di‐Alkylated Ring‐Fused Quinazolinones

Chemistry - A European Journal (2023)

Hongli Wu Weikang Zhang Cancan Zhang Ling‐Tao Wang Wenhui Yang

Abstract Chemodivergent tandem radical cyclization offers exciting possibilities for the synthesis of structurally diverse cyclic compounds. Herein, we revealed a chemodivergent tandem cyclization of alkene‐substituted quinazolinones under metal‐ and base‐free conditions, this transformation is initiated by alkyl radicals produced from oxidant‐induced α ‐C(sp 3 )−H functionalization of alkyl nitriles or esters. The reaction resulted in the selective synthesis of a series of mono‐ and di‐alkylated ring‐fused quinazolinones by modulating the loading of oxidant, reaction temperature, and reaction time. Mechanistic investigations show that the mono‐alkylated ring‐fused quinazolinones is constructed by the key process of 1,2‐hydrogen shift, whereas the di‐alkylated ring‐fused quinazolinones is mainly achieved through crucial steps of resonance and proton transfer. This protocol is the first example of remote second alkylation on the aromatic ring via α ‐C(sp 3 )−H functionalization and difunctionalization achieved by association of two unsaturated bonds in radical cyclization.

Alkene

Tandem

Cascade reaction

Radical cyclization

10.1002/chem.202301390

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Citations (6)

CCDC 1585309: Experimental Crystal Structure Determination

The Cambridge Structural Database (2018)

Ying Wang Chuan-Dong Wei Guo‐Ping Ge Sui Wang Yun‐Xiao Liang

10.5517/ccdc.csd.cc1q6n0l

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Citations (0)

Yellow organic light-emitting diodes based on phosphorescent iridium(III) pyrazine complexes: Fine tuning of emission color

Inorganica Chimica Acta (2008)

Guo‐Ping Ge Guolin Zhang Haiqing Guo Yutao Chuai Dechun Zou

Pyrazine

Quantum Efficiency

10.1016/j.ica.2008.10.001

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Citations (20)

(Acetylacetonato-κ²O,O′)bis[2-(5-methyl-3-phenylpyrazin-2-yl-κN¹)phenyl-κC¹]iridium(III)

Acta Crystallographica Section E Structure Reports Online (2012)

Guo‐Ping Ge Chunyan Li Cheng-Hao Gu Mao-He Li XU Xiao-nan

In the title complex, [Ir(C(17)H(13)N(2))(2)(C(5)H(7)O(2))], the Ir(III) atom is hexa-coordinated in a distorted octa-hedral geometry by two C,N-bidentate 2-(5-methyl-3-phenyl-pyrazin-2-yl)phenyl (mdpp) ligands and one O,O-bidentate acetyl-acetonate ligand. The dihedral angles between the phenyl rings and the pyrazine ring are 9.56 (14) and 58.99 (14)° for one mdpp ligand and 9.34 (14) and 79.94 (15)° for the other.

Pyrazine

Dihedral angle

HEXA

10.1107/s1600536812006022

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Morphological description and statistical characteristic simulation of cocoon filament size curve

Journal of Physics Conference Series (2021)

Pengmin Yang Wane Ning Jiwei Huang Guo‐Ping Ge

Abstract Computer simulation of silk reeling is an important means to understand structure and formation of raw silk, and simulation to generate cocoon filament size curve is the premise of computer simulation of reeling silk. In this paper, according to unique pattern of cocoon filament size curve that is “thin-thick-thin, the last part is the thinnest”, a simulation and generation method of cocoon filament size curve with adjustable morphological is obtained by analyzing the characteristic point values and statistical data of cocoon filament size curve, such as head end size, maximum size and its position on cocoon filament, length of cocoon filament. Through a lot of simulation practice and analysis on statistical characteristics of cocoon filament size curve, it is considered that the proposed generation method has good applicability.

Curve fitting

10.1088/1742-6596/1903/1/012042

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CCDC 1043237: Experimental Crystal Structure Determination

The Cambridge Structural Database (2016)

Guo‐Ping Ge Chuan-Dong Wei Chunyan Li Yun‐Xiao Liang Hongze Liang

10.5517/ccdc.csd.cc140ktj

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Copper-catalyzed multicomponent cascade synthesis of polyfunctionalized β-ketone sulfones

Organic Chemistry Frontiers (2023)

Chun‐Mei Luo Yongbin Sun Ling‐Tao Wang Nan‐Nan Dai Jiao‐Zhe Li

Polyfunctionalized β-ketone sulfones are prepared in one-pot through a series of processes including radical relay, radical addition, hydrogen abstraction, hydrolysis or oxidation.

Hydrogen atom abstraction

10.1039/d3qo00683b

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Citations (8)