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Synthesis of enamines via the Cross-coupling of Thioamides and Diarylketones Promoted by the Sm/SmI_(2)Mixed Reagent

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Chinese Chemical Letters 2006年第1期17卷 1-4页

作者： Wei Min ZHU Zhi Fang LI Yong Min ZHANG Department of Chemistry Zhejiang University Xixi Campus Hangzhou 310028 State Key Laboratory of Organometallic Chemistry Shanghai Institute of Organic Chemistry Chinese Academy of Sciences Shanghai 200032

enamines, promoted by the samarium/samarium diiodide mixed reagent, were synthesized via the cross-coupling of thioamides and diarylketones in good yields.

关键词： Samarium enamines cross-coupling thioamides diarylketones.

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Pd（Ⅱ）-Catalyzed Phosphorylation of Enamido C（sp^2）-H Bonds： A General Route to β-Amido-vinylphosphonates

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Chinese Journal of Chemistry 2018年第9期36卷 809-814页

作者： Baokun qiao Hao-qiang Cao Yin-Jun Huang Yue Zhang Jing Nie Fa-Guang Zhang Jun-An Ma Department of Chemistry Tianjin Key Laboratory of Molecular Optoelectronic Sciences and Tianjin Collaborative Innovation Center of Chemical Science & Engineering Tianjin University Tianjin 300072 China

Organophosphorus compounds are essential structures in modern pharmaceutical, agrochemical, and material sciences. The development of new and efficient methods for the synthesis of C-P bonds has been an important focus of research. We herein report a Pd-catalyzed enamido C（sp2）-H phosphorylation for direct construction of C-P bonds under simple and convenient conditions without the need for additional ligands or directing groups. The present reaction can tolerate a wide range of functional groups, and furnish a variety of phosphorylation products including tetrasubstituted-vinyl β-aminophosphonates that are otherwise difficult to access. This protocol was also exemplified into the late-stage modification of bioactive natural prod- ucts and was suitable for large-scale synthesis.

关键词： C-H activation phosphorylation palladium catalysis enamines late-stage functionalization

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Metal-free Synthesis of Polycarbonyl Pyrroles via K2S2O8-Mediated Oxidative Cyclization of enamines

Metal-free Synthesis of Polycarbonyl Pyrroles via K2S2O8-Med...

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中国化学会第十三届全国有机合成化学学术研讨会

作者： Gao Peng Wang Juan Bai Zijing Shaanxi Key Laboratory of Phytochemistry College of Chemistry and Chemical EngineeringBaoji University of Arts and Sciences

Polysubstituted pyrroles are an important class of five-membered heterocycles existed in numerous natural products and bioactive molecules.Notably,carbonyl groups in these molecules are key moieties which are closely related to their biological activities.Although a variety of enamines successfully converted to carbonyl pyrroles,problems associated with these methods,such as stoichiometric use of expensive hypervalent iodine reagents and transition metals,narrow scope of substrates,and harsh reaction conditions inhibited their further application.Therefore,the practical synthesis of polycarbonyl pyrroles still of great significance,especially less-studied tetracarbonyl pyrroles.Herin,a KSO-promoted radical oxidative cyclization of enamines has been described.A variety of enamines bearing diverse functional groups and substitution patterns react well using KSO as the oxidant without addition of any external catalyst.This protocol provides a very simple route to polycarbonyl pyrroles with advantages including readily available starting materials,mild reaction conditions and wide substrates scope.

关键词： transition metal-free oxidative cyclization enamines polycarbonyl pyrroles

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Palladium-Catalyzed Carbonylation of C-H Bonds for the Synthesis of Carbonyl Compounds

Palladium-Catalyzed Carbonylation of C-H Bonds for the Synth...

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中国化学会第十四届全国有机合成化学学术研讨会

作者： Zheng-Hui Guan Department of Chemistry & Materials Science Northwest University

Carbonylation reactions have proven to be powerful tools for construction of carbonyl compounds. However, transition metal catalyzed carbonylation of C-H bonds with CO remains challenging. In recent years, we have developed palladium-catalyzed carbonylation reactions of various anilines and enamides. Especially, palladium-catalyzed C-H/N-H double carbonylation of secondary alkyl anilines was developed for straightforward synthesis of isatoic anhydrides, and carbonylation of alkenyl C-H bonds of enamides was developed for the synthesis of 1,3-oxazin-6-ones. Furthermore, palladium-catalyzed carbonylative Suzuki-Miyaura coupling of indole and phenyl boronic acid in the presence of I was developed for the synthesis of indol-3-yl aryl ketones. Very recently, palladium-catalyzed regioselective oxidative carbonylation of tri-substituted alkenes with CO and alcohols for the synthesis of α,β-unsaturated esters has been developed. The experiment results and DFT calculations suggested that the oxidative carbonylation proceeded through alkoxylation of palladium catalyst, CO and alkenyl C=C double bond migratory insertion, β-(N)H elimination and tautomerization cascade steps.

关键词： palladium-catalyzed carbonylation enamines C-H activation

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