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Isocyanide-Based One-Pot Cascade Synthesis of 3-Acyl Isoindolinones

Chinese Journal of Chemistry 2024年第3期42卷 259-263页

作者： Jia Liu Yi-Ming Zhu Xiao-Ping Xu Shun-Jun Ji Key Laboratory of Organic Synthesis of Jiangsu Province College of ChemistryChemical Engineering and Materials Science & Collaborative Innovation Center of Suzhou Nano Science and TechnologySoochow UniversitySuzhouJiangsu215123 China Suzhou Baolidi Functional Materials Research Institute SuzhouJiangsu215144 China

A series of 3-acyl-substituted isoindolinone derivatives were synthesized in a one-pot manner via the reaction of o-bromobenzaldehydes,isocyanides,and carboxylic acids in the presence of palladium catalyst and base. The reaction employing easily available starting materials features simple operation and high efficiency. The mechanistic study showed that the reaction might undergo 1) pd-catalyzed [3+2] cyclization of o-bromobenzaldehyde with isocyanide and the re-insertion of another molecule of isocyanide,2) addition of carboxylic acid to in situ formed ketenimine followed by a rearrangement relay to give 3,3-diacyl-substituted isoindolinone derivative. Further transformations of the obtained products through decarbonylation could also be realized.

关键词： One-pot reaction Isocyanide pd catalysis Rearrangement reaction Isoindolinone

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Asymmetric α-Pentadienylation of β-Ketocarbonyls and Aldehydes by Synergistic pd/Chiral Primary Amine catalysis

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Chinese Journal of Chemistry 2023年第24期41卷 3533-3538页

作者： Chang You Sanzhong Luo Center of Basic Molecular Science Department of ChemistryTsinghua UniversityBeijing100084 China

Direct alkylation with skipped enynes or cyclopropropylacetylenes represents an ideal process for the installation of pentadienyl group in terms of atom- and step-economy.The development of catalytic asymmetric versions has been frequently pursued and most of the successes have been achieved with enolizable aldehydes.We herein describe a synergistic chiral primary amine/pd catalysis for asymmetric α-pentadienylation of β-ketocarbonyls and aldehydes with skipped enynes or cyclopropropylacetylenes.The reaction features the construction of acyclic all-carbon quaternary centers with high enantioselectivity,and good functional group tolerance and scalability.

关键词： α-Pentadienylation Synergistic catalysis Chiral primary amine pd catalysis Hydrocarbons

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Developments and applications of allyl-(aza)allyl coupling reactions

绿色合成与催化(英文)

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绿色合成与催化(英文) 2023年第3期4卷 190-205页

作者： Leiyang Lv Huijun Qian Key Laboratory of Advanced Light Conversion Materials and Biophotonics Department of ChemistryRenmin University of ChinaBeijing 100872China

We have summarized the developments and advancements of allyl-(aza)allyl coupling reactions in the past years.Since the first report in 1980,pd-catalyzed allyl-allyl couplings have not drawn chemists'much attention for almost 20 years.Not until the last two decades,transition-metal-catalyzed allyl-(aza)allyl transformations have been retrieved vital interest and significantly developed in many respects,including metal-catalyst,ligand development,mechanistic understanding,substrate scope,and applications in the preparation of complex functional molecules.This review is organized according to the transition metals used in allyl-allyl coupling reactions including our own work.Besides,transition-metal-free,allyl-azaallyl cross-couplings and applications in the total synthesis of natural products and drugs have also been included.

关键词： Allylation pd catalysis Cross-coupling C-C bond formation C-X bond formation

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Synthesis of (+) or (-)-2-(8′-Diphenylphosphino-1′-naphthyl)oxazoline Ligands and Their Application in pd-Catalyzed Allylic Alkylation Reaction

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Chinese Journal of Chemistry 2002年第11期20卷 1363-1368,1131页

作者：麻生明段德慧 State Key Laboratory of Organometallic Chemistry Shanghai Institute of Organic Chemistry Chinese Academy of Sciences Shanghai 200032 China

We synthesized optically active 2-(8′-diphenylphosphino-1′-naphthyl)oxazoline ligands by palladium-catalyzed coupling reactions of (trimethylsilyl)diphenylphosphine with 2-(8′-bromo-1′-naphthyl)oxazolines, which, in turn, were prepared from 8-bromo-1-naphthoyl chloride by the reaction with natural optical active amino alcohols. pd-Catalyzed allylic alkylation reaction induced by these chiral ligands gave the allylic substituted products in high yields and moderate ee values.

关键词： diphenylphosphino-1′-naphthyl)oxazoline pd catalysis allylic alkylation

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Oxidative cyclopalladation triggers the hydroalkylation of alkynes

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Chinese Chemical Letters 2023年第10期34卷 146-152页

作者： Kangbao Zhong Shihan Liu Xiaoqian He Hao Ni Wei Lai Wenting Gong Chunhui Shan Zhuang Zhao Yu Lan Ruopeng Bai School of Chemistry and Chemical Engineering Chongqing Key Laboratory of Theoretical and Computational ChemistryChongqing UniversityChongqing 400030China College of Chemistry and Institute of Green CatalysisZhengzhou UniversityZhengzhou 450001China College of Chemistry Chongqing Normal UniversityChongqing 401331China

This report describes the oxidative cyclopalladation activation of a C≡C bond during the pd-catalyzed hydroalkylation of alkynes and analyzes potential reaction pathways based on density functional theory calculations. The more favorable pathway in-volves an oxidative cyclopalladation to generate a palladacyclopropene intermediate, which is rarely examined in pd-catalyzed alkyne transformations. The reaction pathway proposed herein is kinetically favorable relative to the commonly proposed alkyne insertion mode. Furthermore, the Laplacians of the electron density, interaction region indicators, Mayer bond orders, and localized orbital bonding are evaluated to determine the reaction processes and characterize the key intermediates. Theoretical calculations indicate covalent bonding between a pd(II) center and the two C-atoms in three-membered palladacycle species. Finally, electrostatic potential analysis reveals that the regioselectivity is governed by the charge distribution on the palladacycle moiety during the protonation step.

关键词： pd catalysis Alkynes activation Hydrazones activation Oxidation state DFT

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Recent advances in theoretical studies on ligand-controlled selectivity of nickel-and palladium-catalyzed cross-coupling reactions

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Chinese Chemical Letters 2021年第1期32卷 319-327页

作者： Mengna Cao Hujun Xie Department of Applied Chemistry Zhejiang Gongshang UniversityHangzhou 310018China

Nickel-and palladium-catalyzed cross-coupling reactions have attracted wide attentions,while ligandcontrolled selectivity in these reactions are still elusive,and calculations can help obtain possible catalytic cycles to generate different products and provide insights into key factors of selectivity,which facilitates the development of new catalyst systems to control reaction selectivity.This review covers our efforts and some significant achievements from other groups on ligand-controlled reaction selectivity of coupling reactions,including introduction,computational methods,selectivity control by ligands in Niand pd-catalyzed coupling reactions,as well as summary and future perspectives.

关键词： DFT calculations pd catalysis Ni catalysis Selectivity Reaction mechanism Ligand

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Palladium-catalyzed C-H bond functionalization of （hetero）arenes

Palladium-catalyzed C-H bond functionalization of （hetero）...

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中国化学会·第十六届全国有机合成化学学术研讨会

作者： Jing Sun He Wang Jing-Yun Wang Lei Li 周明东 School of Chemistry and Materials Science Liaoning Shihua University 辽宁石油化工大学

Functionalization of aromatic compounds is an important research issue in organic synthesis.One of the major goal is to develop efficient,regioselective and step-economic methodologies for C-H bond activation of arenes.Nevertheless,due to the intrinsic electronic nature of arene and its substituent（s）,the functionalization of arenes using traditional electrophilic or nucleophilic substitution approaches always require multiple steps,utilize toxic organometallic reagent and generate significant amount of waste/byproducts.The direct C-H bond functionalization has been recognized as a promising method to synthesize useful organic compounds from inert molecules in the fields of organic synthesis,materials science,and pharmaceuticals.In particular,more attentions have been paid to the chelation-assisted transition-metal-catalyzed C-H bond functionalization to construct various C-C or C-X（N,O,S） bonds.Recently,our group have focused on the palladium-catalyzed selective C-H bond activations to construct various（hetero）arenes,mainly including（a） pd（Ⅱ）-catalyzed CS alkenylation of 2-acylpyrroles,（b） pd（Ⅱ）-catalyzed C-H alkenylation of alkyl chain-substituted tetrathienoacene,（c） pd（Ⅱ）-catalyzed sitc-selective C-H bond activation of 2-phenylpyridine N-oxides,（d） meta-selective C-H alkenylation of phenols and（e）meta-selective C-H alkenylation/acetoxylation of arylacetic acid.Therefore,we wish to report the primary results of these work herein.

关键词： pd catalysis C-H activation (hetero)arenes

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Palladium-Catalyzed Asymmetric Hydrophosphorylation of Norbornenes

Palladium-Catalyzed Asymmetric Hydrophosphorylation of Norbo...

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中国化学会第28届学术年会

作者： Qing Xu ab and Li-Biao Han ,a a National Institute of Advanced Industrial Science and Technology(AIST),Tsukuba,Ibaraki 305-8565,Japan, b College of Chemistry and Materials Engineering,Wenzhou University,Wenzhou 325035

＜正＞Chiral organophosphorus compounds are highly useful in biochemistry,organic synthesis,and asymmetric catalysis.However,successful enantioselective preparation of these compounds via metal-catalyzed asymmetric addition of H-P bonds to alkenes is limited.Unlike other H-phosphonates,which can not undergo metal-catalyzed addition to a

关键词： H-Phosphonates Asymmetric Hydrophosphorylation Norbornenes Chiral Organophosphorus Compounds pd catalysis

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Palladium-catalyzed C-H bond functionalization of（hetero）arenes

Palladium-catalyzed C-H bond functionalization of（hetero）a...

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中国化学会第十六届全国均相催化学术会议

作者： Jing Sun He Wang Jing-Yun Wang Lei Li 周明东 School of Chemistry and Materials Science Liaoning Shihua University 辽宁石油化工大学化学与材料科学学院

＜正＞The direct C-H bond functionalization has been recognized as a promising method to synthesize useful organic compounds from inert molecules in the fields of organic synthesis, materials science, and pharmaceuticals. In particular, more attentions have been paid to the chelation-assisted transition-metal-catalyzed C-H bond functionalization to construct various C-C or C-X （N, O, S） bonds.

关键词： pd catalysis C-H activation (hetero)arenes

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