☆ 4.7 Article

Palladium-Catalyzed Oxidative C?C Bond Cleavage Cyclization of Biaryl-2-amines with Alkenes Involving C?H Olefination and Carboamination

ADVANCED SYNTHESIS & CATALYSIS (2012)

Journal

ADVANCED SYNTHESIS & CATALYSIS

Volume 354, Issue 2-3, Pages 347-353

Publisher

WILEY-V C H VERLAG GMBH

DOI: 10.1002/adsc.201100651

Keywords

alkenes; biaryl-2-amines; oxidative C?C bond cleavage; palladium; phenanthridines

Categories

Chemistry, Applied Chemistry, Organic

Funding

Natural Science Foundation of China [20872112]
Hunan University

Ask authors/readers for more resources

Protocol

Community support

Reagent

Community support

Abstract

A new, general method for the synthesis of phenanthridines has been developed by palladium-catalyzed oxidative remote C?H olefinationcarboaminationC?C bond cleavage tandem reaction. It is noteworthy that alkenes are used as the one-carbon resources for this tandem reaction.

Authors

I am an author on this paper

Click your name to claim this paper and add it to your profile.

Reviews

Primary Rating

4.7

Not enough ratings

Secondary Ratings

Novelty

-

Significance

-

Scientific rigor

-

Rate this paper

Recommended

Article Chemistry, Multidisciplinary

Selective C(sp3)-N Bond Cleavage of N,N-Dialkyl Tertiary Amines with the Loss of a Large Alkyl Group via an SN1 Pathway

Jiaoyu Wu, Linqiang Li, Mengtian Liu, Lu Bai, Xinjun Luan

Summary: A novel Pd-0-catalyzed [2+2+1] annulation was proposed for the rapid assembly of tricyclic indoles in a single-step transformation. Experimental results showed that large tert-butyl and benzyl groups were selectively cleaved via an S(N)1 pathway in the presence of smaller alkyl groups.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2022)

Add to Collection

Article Chemistry, Multidisciplinary

Selective Alkynylallylation of the C-C σ Bond of Cyclopropenes

Zeqi Jiang, Sheng-Li Niu, Qiang Zeng, Qin Ouyang, Ying-Chun Chen, Qing Xiao

Summary: A novel Pd-catalyzed reaction has been developed for selective alkynylallylation of specific C-C sigma bonds in cyclopropenes, providing an efficient approach to highly functionalized dienynes. The reaction features fascinating atom and step economy and can produce gram-scale products using a simple, neutral, and low-cost catalytic system with high TONs. DFT calculations suggest that the success of the reaction relies on the selective insertion of cyclopropene double bonds into the C-Pd bond of ambidentate Pd complex and subsequent nonclassical beta-C elimination.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

Add to Collection

Article Chemistry, Organic

Indolizine synthesis via radical cyclization and demethylation of sulfoxonium ylides and 2-(pyridin-2-yl)acetate derivatives

Kexin Su, Xin Guo, Liangwei Zhu, Yafeng Liu, Yixuan Lu, Baohua Chen

Summary: A novel radical cross-coupling/cyclization method has been developed for the straightforward synthesis of structurally diverse methylthio-substituted indolizine compounds. In this process, sulfoxonium ylides undergo disproportionation to produce a new type of indolizine derivative, revealing that DMSO does not drop off from sulfoxonium ylides.

ORGANIC CHEMISTRY FRONTIERS (2021)

Add to Collection

Article Chemistry, Organic

Pd-Catalyzed Alkene Diamination Reactions with O-Benzoylhydroxylamine Electrophiles: Evidence Supporting a Pd(II/IV) Catalytic Cycle, the Role of 2,4-Pentanedione Derivatives as Ligands, and Expanded Substrate Scope

Janelle K. Kirsch, Gabriel A. Gonzalez, Mason S. Faculak, John P. Wolfe

Summary: This article discusses continued studies on Pd-catalyzed alkene diamination reactions, introducing new mechanistic hypothesis and discoveries, demonstrating the importance of Pd ligand selection, and coupling of different amine reactants under new conditions.

JOURNAL OF ORGANIC CHEMISTRY (2021)

Add to Collection

Article Chemistry, Multidisciplinary

Rhodium-Catalyzed Dealkenylative Arylation of Alkenes with Arylboronic Compounds

Guangying Tan, Mowpriya Das, Ivan Maisuls, Cristian A. Strassert, Frank Glorius

Summary: The rhodium-catalyzed dealkenylative arylation of alkenes with arylboronic compounds provides an unconventional access to bi(hetero)aryls with excellent chemoselectivity. This method enables the cleavage of C(aryl)-C(alkenyl) and C(alkenyl)-C(alkenyl) bonds in various alkenes and 1,3-dienes, leading to the efficient construction of novel organic fluorescent molecules with excellent photophysical properties.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

Add to Collection

Article Chemistry, Multidisciplinary

Intragenomic Decarboxylation of 5-Carboxy-2′-deoxycytidine

Eva Korytiakova, Andreas Reichl, Markus Mueller, Thomas Carell

Summary: Cellular DNA consists of four canonical nucleosides and 5-methylcytosine, with stem cells' genome containing three additional dC derivatives formed through oxidation reactions. These derivatives are believed to undergo a cycle of methylation, oxidation, and conversion back to dC within the genome.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

Add to Collection

Article Chemistry, Organic

Iron-catalyzed radical cascade cyclization of oxime esters with isocyanides: synthesis of 1-cyanoalkyl isoquinolines and 6-cyanoalkyl phenanthridines

Dengqi Xue, Rongqi Liu, Denggao Zhang, Ning Li, Yijie Xue, Qianwei Ge, Liming Shao

Summary: An iron-catalyzed radical cascade cyclization has been developed for the synthesis of 1-cyanoalkyl isoquinolines and 6-cyanoalkyl phenanthridines, showing excellent functional group tolerance and broad substrate scope to obtain a diverse range of potentially valuable products in moderate to good yields.

ORGANIC & BIOMOLECULAR CHEMISTRY (2021)

Add to Collection

Article Biochemistry & Molecular Biology

A Chiral Relay Race: Stereoselective Synthesis of Axially Chiral Biaryl Diketones through Ring-Opening of Optical Dihydrophenan-threne-9,10-diols

Lei Shi, Jiawei Zhu, Biqiong Hong, Zhenhua Gu

Summary: In this study, a point-to-axial chirality transfer reaction of optical dihydrophenanthrene-9,10-diols was reported for the synthesis of axially chiral diketones. Two sets of conditions, basic tBuOK/air atmosphere and acidic NaClO/n-Bu4NHSO4, were developed to achieve oxidative cleavage of the C-C bond, leading to the formation of axially chiral biaryl diketones. Finally, the synthetic applications of the obtained chiral aryl diketones were demonstrated briefly.

MOLECULES (2023)

Add to Collection

Article Chemistry, Organic

Allylic Amination of Highly Substituted Alkenes Enabled by Photoredox Catalysis and Cu(II)-Mediated Radical-Polar Crossover

Grace A. Lutovsky, Ellie F. Plachinski, Nicholas L. Reed, Tehshik P. Yoon

Summary: A method for allylic amination using photoredox activation and Cu(II)-mediated radical-polar crossover is described. This strategy allows the synthesis of a range of structurally varied allylic amines. The regioselectivity of this process complements that of conventional methods for allylic amination.

ORGANIC LETTERS (2023)

Add to Collection

Article Chemistry, Multidisciplinary

C-H Bond Functionalization of Aryl Acids and Amines by 'On-water' Reaction: Bi-dentate Directing Group Enabled Synthesis of Biaryl and m-Teraryl Carboxamides

Ashutosh Verma, Anil J. Elias

Summary: In this study, a palladium-catalyzed 'on-water' methodology for the synthesis of biaryl and m-teraryl derivatives of aryl carboxamides by selective mono and bis C-H bond functionalization is reported. The reaction was carried out using 8-aminoquinoline and 2-thiomethylaniline as directing groups and water as the solvent, resulting in high yields of the functionalized products. The insoluble nature of the products in water allowed for the reusability of the solvent and catalyst.

CHEMISTRY-AN ASIAN JOURNAL (2023)

Add to Collection

Article Chemistry, Organic

Copper Catalyzed Direct Synthesis of Unsymmetrically Substituted Oxalamides From Bromodifluoroacetamide and Tertiary Amines

Hongtai Chen, Lianxin Wang, Yujie Liu, Minjie Guo, Wentao Zhao, Xiangyang Tang, Guangwei Wang

Summary: An efficient method utilizing bromodifluoroacetamide and tertiary amines has been developed for the synthesis of unsymmetrical oxalamides under mild reaction conditions, providing a convenient and straightforward strategy for the rapid construction of various unsymmetrically N-substituted oxalamides moieties in a single step.

ASIAN JOURNAL OF ORGANIC CHEMISTRY (2021)

Add to Collection

Article Chemistry, Physical

Pd(II)-Catalyzed C=C Bond Cleavage by a Formal Group-Exchange Reaction

Runyou Ye, Maoshuai Zhu, Xufei Yan, Yang Long, Ying Xia, Xiangge Zhou

Summary: This study reveals a chelation-assisted palladium-catalyzed C=C bond cleavage reaction to form alkenyl nitrile, based on a formal group-exchange reaction. The isolated active Pd(II) complex and deuterium-labeled experiment confirm the necessity of the chelation group, proposing a plausible catalytic pathway.

ACS CATALYSIS (2021)

Add to Collection

Article Chemistry, Multidisciplinary

Experimental and Computational Studies of the Iron-Catalyzed Selective and Controllable Defluorosilylation of Unactivated Aliphatic gem-Difluoroalkenes

Huan Zhang, Enhui Wang, Shasha Geng, Zhengli Liu, Yun He, Qian Peng, Zhang Feng

Summary: The iron-catalyzed defluorosilylation reaction is an efficient, highly functional-group compatible, and stereo- and regioselective reaction that can be used for late-stage silylation of biologically relevant compounds, offering opportunities for applications in medicinal chemistry.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

Add to Collection

Article Chemistry, Organic

Axially Chiral N,N-Ligand-Promoted Pd-Catalyzed Enantioselective Allylic Amination and Alkylation

Miaomiao Liu, Xiaotao Zhang, Rongrong Bao, Fangtao Xiao, Shouyi Cen, Zhipeng Zhang

Summary: An axially chiral N,N-ligand derived from a BINOL-based skeleton and phenanthroline is found to promote Pd-catalyzed asymmetric allylic amination and alkylation of allyl acetates. The reaction is compatible with various amine substrates and affords chiral products with high yield and enantiomeric excess.

ORGANIC LETTERS (2023)

Add to Collection

Article Chemistry, Inorganic & Nuclear

M(II) (M =Cu, Ni) Assisted C-S Bond Cleavage and Oxidative Dehydrogenation of Amine on Non-Innocent Salen Type Ligand Platforms by Varying Nitrogen vs. Sulfur Coordination Atoms

Jayanta Bag, Souvik Barman, Biplab K. Maiti, Kuntal Pal

Summary: In this study, two newly synthesized salen-type ligands were investigated for their metal mediated non-innocence chemistry. Ligand H2L1 showed C-S bond cleavage upon metallation and formed a stable metal complex, while ligand H4L2 underwent slow oxidation via C-H bond activation under aerobic conditions. The results provide insights into the reactivity of these ligands and their potential applications.

EUROPEAN JOURNAL OF INORGANIC CHEMISTRY (2022)

Add to Collection

Article Chemistry, Multidisciplinary

Metal-free nitrative cyclization of N-aryl imines with tert-butyl nitrite: dehydrogenative access to 3-nitroindoles

Guo-Bo Deng, Jia-Ling Zhang, Yan-Yun Liu, Bang Liu, Xu-Heng Yang, Jin-Heng Li

CHEMICAL COMMUNICATIONS (2015)

Add to Collection

Article Chemistry, Applied

Copper-Mediated 1,2-Difunctionalization of Styrenes with Sodium Arylsulfinates and tert-Butyl Nitrite: Facile Access to α-Sulfonylethanone Oximes

Ji Yang, Yan-Yun Liu, Ren-Jie Song, Zhi-Hong Peng, Jin-Heng Li

ADVANCED SYNTHESIS & CATALYSIS (2016)

Add to Collection

Article Multidisciplinary Sciences

Oxidative 1,2-carboamination of alkenes with alkyl nitriles and amines toward γ-amino alkyl nitriles

Yan-Yun Liu, Xu-Heng Yang, Ren-Jie Song, Shenglian Luo, Jin-Heng Li

NATURE COMMUNICATIONS (2017)

Add to Collection

Article Chemistry, Applied

Synthesis of 5-(Fluoromethyl)-4,5-dihydroisoxazoles by Silver-Catalyzed Oxyfluorination of Unactivated Alkenes

Yan-Yun Liu, Ji Yang, Ren-Jie Song, Jin-Heng Lia

ADVANCED SYNTHESIS & CATALYSIS (2014)

Add to Collection

Article Chemistry, Multidisciplinary

Silver-mediated radical cyclization: construction of Delta(2)-isoxazolines from alpha-halo ketoximes and 1,3-dicarbonyl compounds

Yan-Yun Liu, Xu-Heng Yang, Ji Yang, Ren-Jie Song, Jin-Heng Li

CHEMICAL COMMUNICATIONS (2014)

Add to Collection

Article Chemistry, Organic

Palladium-Catalyzed Conjugate Addition to Electron-Deficient Alkynes with Benzenesulfinic Acid Derived from 1,2-Bis(phenylsulfonyl)ethane: Selective Synthesis of (E)-Vinyl Sulfones

Ren-Jie Song, Yu Liu, Yan-Yun Liu, Jin-Heng Li

JOURNAL OF ORGANIC CHEMISTRY (2011)

Add to Collection

Article Chemistry, Organic

Palladium-Catalyzed Methylation of Alkynyl C(sp)-H Bonds with Dimethyl Sulfonium Ylides

Yan-Yun Liu, Xu-Heng Yang, Xiao-Cheng Huang, Wen-Ting Wei, Ren-Jie Song, Jin-Heng Li

JOURNAL OF ORGANIC CHEMISTRY (2013)

Add to Collection

Article Chemistry, Organic

Synthesis of 2,4-Bis(aryloxy)-1,5-diarylpentane-1,5-diones by Base-Mediated Tandem Reaction

Ren-Jie Song, Yan-Yun Liu, Ji-Cheng Wu, Yu Liu, Guo-Bo Deng, Xiao-Xu Qi, Ye-Xiang Xie, Lu-Bin Gong, Wei Liu, Jin-Heng Li

SYNTHESIS-STUTTGART (2012)

Add to Collection

Article Chemistry, Organic

Copper-Catalyzed C(sp 3 )-H Azidation of 1,3-Dihydro-2 H -indol-2-ones Under Mild Conditions

Wen-Hui Bao, Le-Han Gao, Wei-Wei Ying, Wei-Ting Chen, Gan-Ping Chen, Wen-Ting Wei, Yan-Yun Liu, Qiang Li

SYNLETT (2019)

Add to Collection

Article Chemistry, Organic

Radical Heck-type reaction of styrenes with sulfonyl hydrazides on water at room temperature

Wen-Hui Bao, Wei-Wei Ying, Xu-Dong Xu, Guo-Dong Zhou, Xiao-Xiao Meng, Wen-Ting Wei, Yan-Yun Liu, Qiang Li

TETRAHEDRON LETTERS (2019)

Add to Collection

Article Chemistry, Multidisciplinary

A Base- and Ligand-Free Copper-Catalyzed Oxidative Coupling of Terminal Alkyl Alkynes

Wei-Wei Ying, Wen-Hui Bao, Xu-Dong Xu, Yi-Ning Wang, Si-Zhe Song, Hongze Liang, Youren Dong, Wen-Ting Wei, Yan-Yun Liu, Qiang Li

CHEMISTRYSELECT (2019)

Add to Collection

Article Chemistry, Organic

Metal-Free Regioselective Oxynitration of Acrylamides: Synthesis of 1,2-Nitro Alcohols

Le-Han Gao, Xiao-Xiao Meng, Yi-Ning Wang, Si-Zhe Song, Guo-Ping Ge, Youren Dong, Wen-Ting Wei, Yan-Yun Liu, Qiang Li

ASIAN JOURNAL OF ORGANIC CHEMISTRY (2019)

Add to Collection

Article Chemistry, Multidisciplinary

Synthesis of spirocyclic Δ4-isoxazolines via [3+2] cycloaddition of indanone-derived ketonitrones with alkynes

Yilin Liu, Jiaxue Liu, Yan-Yun Liu, Boxiao Tang, Hongwei Lin, Yuanxiang Li, Lin Zhang

Summary: A [3 + 2] cycloaddition reaction of indanone-derived nitrones and alkynes under mild conditions was developed for facile synthesis of spirocyclic indenyl isoxazolines with structural diversity. The sequential generation of in situ ketonitrone from unsaturated ketones and N-alkylhydroxylamines achieved the desired products with moderate to good diastereoselectivity. Additionally, the spirocyclic product could be conveniently transformed into indenyl-based allylic alcohol and enamide.

RSC ADVANCES (2021)

Add to Collection

Article Chemistry, Organic

Mild and efficient copper-catalyzed oxidative cyclization of oximes with 2-aminobenzyl alcohols at room temperature: synthesis of polysubstituted quinolines

Yan-Yun Liu, Yang Wei, Zhi-Hui Huang, Yilin Liu

Summary: A ligand-free Cu-catalyzed protocol for the synthesis of polysubstituted quinolines via the oxidative cyclization of oxime acetates with 2-aminobenzyl alcohols has been developed at room temperature. This method provides good functional group tolerance under mild conditions and can be applied for the preparation of quinolines on a gram scale. Oxime acetates serve as internal oxidants in the reactions, making this method very attractive.

ORGANIC & BIOMOLECULAR CHEMISTRY (2021)

Add to Collection

No Data Available

© Peeref 2019-2024. All rights reserved.