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alkyl radical Initiated Cyclization/Cascade for Synthesizing Lactam-Substituted alkyl Sulfones

Chinese Journal of Chemistry 2024年第16期42卷 1853-1859页

作者： Li-Jun Wu Kai-Yi Zhang Pei Yang Chuan-Chong Peng Jin-Hui Liu Qing Li Da-Zhi Sun Shuangfeng Yin College of Sciences Central South University of Forestry and TechnologyChangshaHunan410004 China School of Chemistry and Chemical Engineering Inner Mongolia UniversityHohhotInner Mongolia010021 China

An alkyl radical initiated cyclization/tandem reaction of alkyl bromides and alkyl electrophiles by using potassium metabisulphite(K_(2)S_(2)O_(5))as a connector is developed for the synthesis of various lactam-substituted alkyl ***,this process does not require a metal catalyst or metal powder reductant,highlighting its environmentally friendly *** reaction demonstrates outstanding substrate adaptability and a high tolerance towards diverse functional ***,the biologically active molecules and commercially available drugs with a late-stage modification are also highly compatible with this *** studies revealed that the reaction proceeds through a single-step process involving intramolecular radical cyclization,"SO_(2)"insertion,and external alkyl incorporation.

关键词： alkyl radical Metal-free catalyzed Cyclization/cascade Potassium metabisulphite Electrophiles alkyl sulfones Lactams alkyl bromides Sodium formate

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alkyl radical Triggered in situ SO2-Capture Cascades

Alkyl Radical Triggered in situ SO2-Capture Cascades

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中国化学会·第十五届全国有机合成化学学术研讨会

作者： Honggui Huang 李毅 Department of Chemistry Fuzhou University 福州大学

Sulfur dioxide(SO) could serve as the most direct and attractive feedstock to synthesize sulfonyl compounds which are of great importance on pharmaceuticals, agrochemicals, materials and synthetic intermediates. However, direct utilization of SO for the synthesis of value-added products was mainly restricted by its notorious toxicity, hard-to-handle gaseous state and amphoteric chemical characteristic;therefore reports on direct SO-involved chemistry in organic synthesis are relatively *** the ongoing work of our recent efforts on radical cascade reactions to construct compounds with multiple rings, we reported an unprecedented in situ SO-capture cascade triggered by alkyl radical(Fig.1-a). Mechanistic investigations suggest that, triggered by alkyl radical, SO was released in situ and subsequently fixed into polycyclic small *** this method, a wide range of alkylsulfonyl substituted polycyclic compounds were easily prepared with high yields and good functional group *** on this strategy, we disclosed recently the construction of sulfonated oxindoles assembled by radical triggered in situ SO-capture cascade(Fig.1-b).

关键词： in situ SO2-capture radical cascade sulfonated oxindoles alkyl radical

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Deoxygenative alkylation of tertiary amides using alkyl iodides under visible light

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Science China Chemistry 2022年第11期65卷 2231-2237页

作者： Feng Zhao Feng Jiang Xiaoming Wang The Education Ministry Key Lab of Resource Chemistry and Shanghai Key Laboratory of Rare Earth Functional Materials College of Chemistry and Materials ScienceShanghai Normal UniversityShanghai 200234China State Key Laboratory of Organometallic Chemistry Center for Excellence in Molecular SynthesisShanghai Institute of Organic ChemistryChinese Academy of SciencesShanghai 200032China School of Chemistry and Materials Science Hangzhou Institute for Advanced StudyUniversity of Chinese Academy of SciencesHangzhou310024China

It is an unceasing goal for organic chemists to develop new catalytic methodologies for functional group transformations of widespread molecular structures. Amides are readily available from simple and reliable reactions, which are common structural units found in biologically active compounds. Consequently, they are attractive to be exploited in amine synthesis by reductive cross coupling. However, deoxygenative functionalization of amides is a long-standing challenge owing to the inertness of the resonance-stabilized amide C=O bond. In this work, a deoxygenative alkylation strategy was demonstrated, which combines amides and alkyl iodides to build structurally diverse tertiary alkylamines in a single step. Compared with previous deoxygenative alkylation of amides using organometallic reagents as functional partner, this work uses stable and easily available alkyl halides as functionalization reagents. The versatile and flexible strategy plus structural and functional diversity of readily available amides and alkyl iodides renders it highly appealing for the streamlined synthesis of tertiary amines and would be of much interest in areas such as pharmaceutical and agrochemical research.

关键词： deoxygenative alkylation amide transformation alkyl radical alkylamine visible light

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Recent advances in synthesis of organosilicons via radical strategies

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Chinese Chemical Letters 2021年第4期32卷 1280-1292页

作者： Xueping Zhang Jingkun Fang Chun Cai Guoping Lu School of Chemical Engineering Nanjing University of ScienceTechnologyNanjing 210094China

Organosilicon compounds play an important role in the fields of materials science,pharmacy,and organic *** development of effective approaches for the preparation of these compounds have also become a research focus in organic *** recent years,free radical synthesis of organosilicons has been vigorously developed,which generally has the advantages of milder synthesis conditions,higher yields and selectivity,and free of precious metal catalysts compared with traditional *** article reviews research progresses in the synthesis of organosilico n compounds by free radical pathways since *** most cases,the radical silylation is achieved based on the reaction of silyl radicals,which are triggered by four routes including peroxide,transition-metal-induced peroxide decomposition,alkali,*** alkyl radicals can also initiate the radical silylation for the generation of C(sp^(3))—Si bonds.

关键词： Organosilicon radical silylation Single electron transfer Hydrogen atom transfer Photoredox alkyl radical

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Degradable Hybrid CuS Nanoparticles for Imaging-Guided Synergistic Cancer Therapy via Low-Power NIR-II Light Excitation

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CCS Chemistry 2021年第5期3卷 1336-1349页

作者： Yidan Sun Hua Shi Xiaoyang Cheng Luyan Wu Yuqi Wang Zhengyang Zhou Jian He Hong-Yuan Chen Deju Ye State Key Laboratory of Analytical Chemistry for Life Science Chemistry and Biomedicine Innovation Center(ChemBIC)School of Chemistry and Chemical EngineeringNanjing UniversityNanjing 210023 Department of Radiology Nanjing Drum Tower HospitalThe Affiliated Hospital of Nanjing University Medical SchoolNanjing 210008

Near-infrared(NIR)-II light-excitable photonic agents capable of generating tumor hyperthermia and cytotoxic free radicals are promising for synergistic phototherapy of ***,the lack of NIR-II excitable agents makes it challenging to achieve combinational tumor ***,the authors have reported on a tumor-targeting and degradable hybrid copper sulfide(CuS)nanoparticle(AIBA@CuS-FA)via loading a hydrophilic Azo initiator(AIBA)into an amphiphilic lipid-encapsulating CuS ***@CuS-FA shows high photothermal conversion efficiency(PCE≈47.5%)at 1064 nm,enabling heat production to trigger tumor hyperthermia and thermal decomposition of AIBA into cytotoxic free alkyl radicals upon irradiation with a 1064-nm laser under low-power density(0.5 W/cm2).Moreover,alkyl radicals can drive degradation of AIBA@CuS-FA and embedded CuS nanodisks,releasing Cu^(2+)ions that can catalyze a Fenton-like reaction for hydroxyl radical(•OH)production to promote tumor *** demonstrate promise for combinational photothermal therapy(PTT),oxygen-independent alkyl radical therapy,and chemodynamic therapy(CDT)of tumors.

关键词： NIR-II copper sulfide alkyl radical synergistic therapy imaging

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