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Metal-Free Arylsulfonyl Radical Triggered Cascade Cyclization of Phenyl-Linked 1,6-enynes:Synthesis of 2,3-Dihydro-1H-indenes and 10a,11-Dihydro-10H-benzo[b]fluorines

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Chinese Journal of Chemistry 2022年第23期40卷 2756-2762页

作者： Lin-Ping Hu De-Run Zhang Xiao-Hong Huang Feng-Lin Liu Xia Li Ming-Yu Teng Guo-Li Huang School of Chemistry and Chemical Engineering Yunnan Normal UniversityKunmingYunnan 650500China Department of Library Yunnan Normal UniversityKunmingYunnan 650500China

Aryl sulfonyl radical triggered cascade cyclization of phenyl-linked 1,6-enynes for the synthesis of biologically important indenes containing alkenyl C—X bonds and 10a,11-dihydro-10H-benzo[b]fluorines is presented.In these radical cascade processes,three new chemical bonds,including C—S,C—C,and C—X bonds,and three C—C bonds are formed in one step.The method is attractive and valuable due to its metal-free,mild reaction conditions,broad substrate scope and good functional group tolerance.

关键词： Radical reactions Cyclization enynes Aryl sulfonyl Indenes

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Ni-catalyzed regiodivergent hydrophosphorylation of enynes

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Chinese Chemical Letters 2023年第6期34卷 301-305页

作者： Sa-Na Yang Shao-Han Sun Chang-Hui Liu Xiang-Ting Min Boshun Wan Ding-Wei Ji Qing-An Chen Dalian Institute of Chemical Physics Chinese Academy of SciencesDalian 116023China University of Chinese Academy of Sciences Beijing 100049China

A regiodivergent hydrophosphorylation of enynes with phosphites has been developed using earthabundant nickel catalyst.The manipulation of regioselectivity can be achieved by regulating the insertion order of alkyne bonds with(RO)_(2)P(O)-Ni-H or R_(2)P(O)O-Ni-H species,respectively.Under the Ni/Xantphos catalysis,4,1-hydrophosphorylation is selectively obtained while the adding of acid can promote reactions towards 1,2-addition.By employing an additional Pd-H catalysis,2,1-hydrophosphorylation is also an accessible task in one-pot reaction.Mechanistic studies and analysis have also been performed to interpret the origin of the regioselective regulation.This work highlights the arts in accessing different regioisomers by diverting common elementary reaction steps.

关键词： Regiodivergent Hydrophosphorylation Nickel catalysis enynes

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Diastereodivergent Hydrosilylative Enyne Cyclization Catalyzed by N-Heterocyclic Carbene-Ni(o)

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Chinese Journal of Chemistry 2021年第6期39卷 1587-1592页

作者： Meng Yu Xuefeng Yong Weiwei Gao Chun-Yu Ho Guangdong Province Key Laboratory of Catalysis Department of ChemistrySouthern University of Science and Technology(SUSTech)1088 Xueyuon AvenueShenzhenGuangdong 518055China Shenzhen Grubbs Institute Deportment of ChemistrySouthern University of Science and Technology(SUSTech)1088 Xueyuan AvenueShenzhenGuangdong 518055China

Catalytic diastereodivergent hydrosilylative enyne cyclization with high generality and broad scope was achieved using electronic ac-tivated N-heterocyclic carbene-Ni(O)as a catalyst and R_(3)SiH as silane(IPr^(Cl),syn-:anti-selectivity from up to 98:2 to 7:93 by Z=0,NH vs.NMs,R^(1)=n-pentyl).Heterocycles bearing homoallylsilane rather than vinylsilane was obtained chemoselectively.The undesired yet highly competitive reactivity was suppressed,like direct hydrosilylation of alkene and alkyne concurrently.Optionally,the homoallylsilane products could be reduced further in one-pot using IPr^(Me) as ligand and(EtO)_(3)SiH as silane under otherwise the same standard condition as the above,offering practical access to additional stereocenters and more diverse product structures from enynes.

关键词： N-Heterocyclic carbenes enynes Diastereodivergent synthesis Hydrosilylation Hydroalkenylation

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Special Issue of ＂Oxidative Radical Reactions＂

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Chinese Journal of Chemistry 2017年第3期35卷 247-247页

作者： Li, Jin-Heng Nanchang Hangkong Univ Key Lab Jiangxi Prov Persistent Pollutants Contro Nanchang 330063 Jiangxi Peoples R China

Radical chemistry has become an important central theme in synthesis that has attracted much attention of the chemical researchers in the last century since Gomberg first prepared the stable triphenylmethyl radical in 1900.However,radical chemistry in organic synthesis had become stagnant over a period of time,probably owing to the requirement of very poisonous reagents as the initiators and uncontrollable selectivity.

关键词： ORGANIC synthesis (Chemistry) enynes RING formation (Chemistry)

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Direct Access to Trifluoromethyl-Substituted Carbamates from Carbon Dioxide via Copper-Catalyzed Cascade Cyclization of enynes

Direct Access to Trifluoromethyl-Substituted Carbamates from...

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中国化学会·第一届全国二氧化碳资源化利用学术会议

作者： Lu Wang Chaorong Qi Ruixiang Cheng Hongjian Liu Huanfeng Jiang Key Laboratory of Functional Molecular Engineering of Guangdong Province School of Chemistry and Chemical EngineeringSouth China University of Technology

Organic carbamates constitute an important class of bioactive compounds, which widely exist in many natural products, pharmaceuticals, and agrochemicals. They could also serve as versatile building blocks in organic synthesis. Recently, CO has emerged as an attractive alternative to phosgene for the synthesis of carbamates because of its advantages such as nontoxicity, natural abundance, and renewability. Many multicomponent reactions involving the use of halohydrocarbons, alcohols, unsaturated hydrocarbons, or other compounds as the coupling partners have been reported for the assembly of carbamates. In recent years, our group has also developed several novel multicomponent reactions for the synthesis of organic carbamates. On the other hand, it is commonly accepted that the incorporation of fluorine or fluorine-containing functional groups into organic compounds could substantially alter their physical and chemical properties, which may be beneficial for improving their biological activities. Herein, we wish to report a copper-catalyzed radical cascade cyclization of enynes with Togni’s reagent in the presence of CO and amines, providing a direct and efficient protocol for the synthesis of a diverse range of trifluoromethylated carbamates, which are difficult to access using existing methods(Figure 1).

关键词： trifluoromethylated carbamates copper-catalyzed carbon dioxide enynes

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