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Copper-Catalyzed carbonylative Synthesis of β-Boryl Amides via Boroamidation of Alkenes

CCS Chemistry 2021年第4期3卷 2643-2654页

作者： Fu-Peng Wu Jens Holz Yang Yuan Xiao-Feng Wu Leibniz-Institut für Katalyse e.V.an der Universität Rostock Rostock 18059 Dalian National Laboratory for Clean Energy Dalian Institute of Chemical PhysicsChinese Academy of SciencesDalian 116023

β-Boryl amide is a class of high value intermediates in organic chemistry.In this work,a copper-catalyzed carbonylative boroamidation of olefins toward the synthesize ofβ-boryl amides has been developed.Several new chemical bonds were constructed in this transformation.A wide range ofβ-boryl amides were produced in excellent regioselectivity and good to excellent yields.Ethylene gas can be successfully transformed under the same standard conditions as well.Notably,with the use of a chiral ligand,the first example of enantioselective carbonylative boroamidation of alkenes was realized.In addition,Piposulfan and Pipobroman,antineoplastic medicines,were prepared by this methodology in a straightforward manner.

关键词： carbonylative boroamidation copper catalyst enantioselective olefins

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Difluoroalkylative carbonylation of alkenes to access carbonyl difluoro-containing heterocycles:convenient synthesis of gemigliptin

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Science China Chemistry 2023年第1期66卷 139-146页

作者： Zhi-Peng Bao Youcan Zhang Le-Cheng Wang Xiao-Feng Wu Dalian National Laboratory for Clean Energy Dalian Institute of Chemical PhysicsChinese Academy of SciencesDalian 116023China Leibniz-Institut für Katalyse e.V.Albert-Einstein-Straße 29a Rostock 18059Germany

Fluorinated heterocycles play a vital role in pharmaceutical and agrochemical industries.Hence,rapid and efficient construction of fluorinated heterocycles remains highly demanded.Herein,a difluoroalkylative carbonylative cyclization of unactivated alkenes and ethylene gas enabled by palladium catalysis has been developed for the first time toward the synthesis ofα-carbonyl difluoro-modified glutarimides.This procedure can also be applied to the synthesis of Ge Migliptin which is a medicine approved for the treatment of type 2 diabetes mellitus.

关键词： difluoroalkylative carbonylative unactivated alkenes ethylene gas heterocycles

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carbonylative Coupling of 4,4’-Diiodobiphenyl Catalyzed by Pd(NHC) Complex

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Green and Sustainable Chemistry 2013年第1期3卷 15-18页

作者： Do-Hun Lee Jung-Tai Hahn Dai-Il Jung Department of Beautycare Youngdong University Youngdong South Korea Department of Chemistry Dong-A University Busan South Korea

To develop a luminescent material with high color purity, luminous efficiency, and stability, we synthesized diketone by carbonylative Suzuki coupling in the presence of Pd(NHC) complex as the catalyst. carbonylative coupling of 4,4’-diiodobiphenyl and phenylboronic acid was investigated to study in detail the catalytic ability of the Pd(NHC) complex. Reactions were carried out using both CO and metal carbonyls. Bis-(1,3-dihydro-1,3-dimethyl-2H-imidazol- 2-ylidene) diiodo palladium was used as the catalytic complex. Reaction products biphenyl-4,4’-diylbis (phenyl- methanone) 3 and (4’-iodobiphenyl-4-yl)(phenyl) methanone 4 were obtained as a result of CO insertion into the palladium(II)-aryl bond. However, when pyridine-4-yl boronic acid was used in place of phenylboronic acid as the starting reagent, synthetic reaction yielding 3 and 4 were found not to occur.

关键词： carbonylative Coupling Metal Carbonyl Pd(NHC) Complex 4 4’-Diiodobiphenyl Phenylboronic Acid

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Cycloadditions of 1-iminylphosphirane complexes with allenes

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Chinese Chemical Letters 2021年第1期32卷 449-452页

作者： Juan Li Mingyue Cui Rongqiang Tian Zheng Duan François Mathey College of Chemistry Green Catalysis CenterInternational Phosphorus LaboratoryInternational Joint Research Laboratory for Functional Organophosphorus Materials of Henan ProvinceZhengzhou UniversityZhengzhou 450001China

A cascade carbonylative ring expansion and [2+2]/[4+2] cycloaddition of strained 1-iminylphosphirane complexes with aryl allenes were reported.The carbonylative ring expansion of 1-iminylphosphirane complexes provides an azaphosphacyclohexone complex intermediate with a C=P double bond.The following [2+2] or dearomatic [4+2] cycloaddition of this intermediate with allenes is modulated by the aryl substituents on the imino carbon.The regioselective [2+2] cycloaddition with 1,1-diarylallene provides an entry to bicyclo[4.2.0]octan-4-one skeletons featuring a four-membered phosphacyclobutane moiety.While dearomatic [4+2] cycloaddition was preferred with less aromatic naphthalene and yielded octahydrochrysene skeleton containing heteroatoms.

关键词： Phosphirane Allene Ring expansion Cycloaddition carbonylative Heterocycle

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