☆ 4.8 Article

Mn-Catalyzed Dehydrocyanative Transannulation of Heteroarenes and Propargyl Carbonates through C-H Activation: Beyond the Permanent Directing Effects of Pyridines/Pyrimidines

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

期刊

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

卷 58, 期 15, 页码 5090-5094

出版社

WILEY-V C H VERLAG GMBH

DOI: 10.1002/anie.201900166

关键词

allenylation; C-H activation; Diels-Alder reactions; directing groups; Manganese

类别

Chemistry, Multidisciplinary

资金

NSFC [21525208]
Fundamental Research Funds for the Central Universities [GK201903028]
SNNU

向作者/读者索取更多资源

Protocol

Reagent

摘要

Pyridines/pyrimidines are common and effective directing groups in C-H activation. However, they are poorly functionalizable heteroarenes. Reported in this work is Mn-catalyzed dehydrocyanative transannulation between three classes of heteroarenes and propargyl carbonates. The pyridyl/pyrimidyl groups in the heteroarenes initially function as directing groups to enable C-H allenylation; they then undergo intramolecular Diels-Alder/retro-Diels-Alder reactions with the allene moiety to afford fused carbo/heterocycles. Three key intermediates at different stages of the reaction were isolated.

作者

我是这篇论文的作者

点击您的名字以认领此论文并将其添加到您的个人资料中。

评论

主要评分

4.8

评分不足

次要评分

新颖性

-

重要性

-

科学严谨性

-

评价这篇论文

推荐

Article Chemistry, Organic

Cross-Coupling Reactions of Monosubstituted Tetrazines

Lukas Hoff, Simon D. Schnell, Andrea Tomio, Anthony Linden, Karl Gademann

Summary: A silver-mediated Pd-catalyzed cross-coupling method for 3-bromo-1,2,4,5-tetrazine with boronic acids was presented in this study. It was found that electronic modification of the dppf ligand played a crucial role in achieving good turnover. Using this fast method, a variety of alkyl-, heteroatom-, and halide-substituted aryl- and heteroaryl-tetrazines were successfully prepared, with yields up to 87%.

ORGANIC LETTERS (2021)

添加到收藏夹

Article Chemistry, Multidisciplinary

PdII-Catalyzed Site-selectiveβ- andγ-C(sp3)-H Arylation of PrimaryAldehydes Controlled by Transient Directing Groups

Yi-Hao Li, Yuxin Ouyang, Nikita Chekshin, Jin-Quan Yu

Summary: Pd(II)-catalyzed site-selective beta- and gamma-C(sp3)-H arylation of primary aldehydes is achieved by rational design of L,X-type transient directing groups (TDG). External 2-pyridone ligands are crucial for the observed reactivity. By minimizing the loading of acid additives, the ligand effect is enhanced to achieve high reactivities of the challenging primary aldehyde substrates. Site selectivity can be switched by changing the bite angle of TDG to match the desired palladacycle size, as supported by experimental and computational investigations.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2022)

添加到收藏夹

Review Chemistry, Physical

Traceless Directing Groups in Sustainable Metal-Catalyzed C-H Activation

Athanasios Zarkadoulas, Ioanna Zgouleta, Nikolaos V. Tzouras, Georgios C. Vougioukalakis

Summary: This review article summarizes the work done on TDG-assisted catalysis with manganese, iron, cobalt, nickel, or copper catalysts, and discusses the structure-activity relationships observed, by presenting the catalytic pathways and range of transformations reported thus far.

CATALYSTS (2021)

添加到收藏夹

Article Chemistry, Organic

Rh(iii)-catalyzed (5+2)-cycloaddition reactions of ortho-hydroxyethyl phenols with internal alkynes: efficient synthesis of benzoxepines

Pratiksha Bhorali, Jyotshna Phukon, Sanjib Gogoi

Summary: An unprecedented (5 + 2)-cycloaddition reaction between ortho-hydroxyethyl phenol and internal alkyne was developed using rhodium(iii) catalysis. This reaction provided benzoxepine derivatives with high biological significance. A wide range of ortho-hydroxyethyl phenols and internal alkynes were effectively used to obtain high yields of benzoxepines.

ORGANIC & BIOMOLECULAR CHEMISTRY (2023)

添加到收藏夹

Article Chemistry, Organic

An Integrated Building Block for Cascade Diels-Alder and Hetero-Diels-Alder Reactions

Shuheng Xu, Linwei Zeng, Sunliang Cui

Summary: The Diels-Alder (DA) reaction and hetero-Diels-Alder (HDA) reaction are powerful methods for constructing carbocycles and heterocycles. This study presents an integrated building block that combines both DA and HDA reactions, utilizing triazenyl dienes to undergo the DA reaction and the newly released alkene moiety and triazene to engage in the HDA reaction.

ORGANIC LETTERS (2022)

添加到收藏夹

Review Chemistry, Multidisciplinary

Decoding Directing Groups and Their Pivotal Role in C-H Activation

Karunanidhi Murali, Luana A. Machado, Renato L. Carvalho, Leandro F. Pedrosa, Rishav Mukherjee, Eufranio N. Da Silva Junior, Debabrata Maiti

Summary: C-H functionalization has made significant advancements in synthetic organic chemistry, offering promising prospects in drug development and molecular architecture. The employment of novel metal catalysts and metal-free organic ligands has enabled selective activation of C-H bonds, overcoming previous challenges faced by chemists.

CHEMISTRY-A EUROPEAN JOURNAL (2021)

添加到收藏夹

Review Chemistry, Applied

Recent Advances in Cobalt-Catalyzed, Directing-Group-Assisted C-H Bond Amidation Reactions

Sereena Sunny, Ramasamy Karvembu

Summary: C-N bond formation reactions have gained significant interest recently due to the prevalence of nitrogen-containing compounds in pharmaceuticals. The use of directing-group-assisted C-H amidation with cobalt as a catalyst has been a focus for its unique properties and efficiency in selective amidation of C-H bonds. The evolution of directing group preferences and their function in site selection have been discussed in recent developments of this field.

ADVANCED SYNTHESIS & CATALYSIS (2021)

添加到收藏夹

Article Chemistry, Multidisciplinary

Palladium(II)-Catalyzed Selective Arylation of Tertiary C-H Bonds of Cyclobutylmethyl Ketones Using Transient Directing Groups

Jin-Tang Cheng, Li-Jun Xiao, Shao-Qun Qian, Zhe Zhuang, An Liu, Jin-Quan Yu

Summary: In this study, we report the first example of selective Pd(II)-catalyzed tertiary C-H activation of cyclobutylmethyl ketones using a transient directing group. An electron-deficient 2-pyridone ligand was identified as the optimal external ligand to achieve tertiary C-H activation. Various cyclobutylmethyl ketones with quaternary carbon centers were obtained in high yields without the need for preinstalling internal directing groups, and showed high regioselectivity for tertiary C-H arylation.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2022)

添加到收藏夹

Article Multidisciplinary Sciences

Electrocatalyzed direct arene alkenylations without directing groups for selective late-stage drug diversification

Zhipeng Lin, Uttam Dhawa, Xiaoyan Hou, Max Surke, Binbin Yuan, Shu-Wen Li, Yan-Cheng Liou, Magnus J. Johansson, Li-Cheng Xu, Chen-Hang Chao, Xin Hong, Lutz Ackermann

Summary: Electrochemistry, with the aid of data science and artificial intelligence, is increasingly being used for molecular synthesis. The authors have successfully utilized electrocatalyzed C-H activations for selective alkenylation in late-stage drug diversification. This approach eliminates the need for directing groups, which simplifies the synthesis process and reduces waste.

NATURE COMMUNICATIONS (2023)

添加到收藏夹

Article Chemistry, Physical

PdII-Catalyzed ?-C(sp3)-H (Hetero)arylation of Ketones Enabled by Transient Directing Groups

Yi-Hao Li, Yuxin Ouyang, Nikita Chekshin, Jin-Quan Yu

Summary: Pd(II)-catalyzed gamma-C(sp3)-H (hetero)arylation of aliphatic ketones using alpha-amino acids as transient directing groups (TDG) has been developed. By reducing the loading of acid additives, the crucial ligand effect of 2-pyridone is enhanced, leading to improved reactivity and the possibility of cyclic gamma-methylene C(sp3)-H arylation of ketones. Mechanistic investigation and comparison to the gamma-C-H arylation of aldehydes provide structural insights for designing site-selective TDGs.

ACS CATALYSIS (2022)

添加到收藏夹

Article Chemistry, Multidisciplinary

Ruthenium(II)-catalyzed para-selective C??H difluoroalkylation of aromatic aldehydes and ketones using transient directing groups

Yaohang Cheng, Yuhang He, Jie Zheng, Hui Yang, Jun Liu, Guanghui An, Guangming Li

Summary: The method developed utilizes Ru(II) catalysis to facilitate the synthesis of challenging difluoroalkylated aldehydes and ketones with para-selectivity.

CHINESE CHEMICAL LETTERS (2021)

添加到收藏夹

Review Chemistry, Organic

Research Progress of Amino Acids as Transient Directing Groups in C-H Bond Activation Reactions

Dong Sifan, Li Haolong, Qin Yuan, Fan Shiming, Liu Shouxin

Summary: In recent years, the TDG-based strategy of C-H activation has gained attention due to its improved efficiency compared to typical C-H activation reactions. Amino acids have been successful TDGs in C-H activation, thanks to their low cost and diverse structures. By controlling the site selectivity and stereo-selectivity through alpha- or beta-amino acids, significant progress has been made in transition-metal-catalyzed C-H bond activation and functionalization. This review summarizes the recent research progress, categorizes it based on different amino acid types, and discusses the limitations and future perspectives of this cutting-edge area.

CHINESE JOURNAL OF ORGANIC CHEMISTRY (2023)

添加到收藏夹

Article Chemistry, Multidisciplinary

Dimerization reactions with oxidized brominated thiophenes

Khaled Youssef, Magali Allain, Thomas Cauchy, Frederic Gohier

Summary: 2-Bromo, 3-bromothiophene, 2,5-dibromothiophene, 3,4-dibromothiophene, and perbrominated thiophene were oxidized under different conditions to form thiophene S,S-dioxide. Depending on the substitution, sulfone was obtained when the hindered thiophene was used. However, monosubstituted thiophenes could not be transformed into sulfone due to the reactivity of the sulfoxide intermediate, which led to dimerization. The structures were confirmed through the obtaining of crystals. The oxidation of 3,4-dibromothiophene could either result in the formation of cycloadduct or the isolation of sulfone, which could further evolve into benzothiophene sulfone.

NEW JOURNAL OF CHEMISTRY (2023)

添加到收藏夹

Article Chemistry, Organic

Base-Promoted [4+2] Annulation Reaction of In Situ-Generated Azadienes from N-Propargylamines with Active Methylene Compounds: Access to Highly Functionalized 2-Pyridones

Bipin Kumar Behera, Pallav Jyoti Arandhara, Bikoshita Porashar, Surjya Kumar Bora, Anil K. Saikia

Summary: A facile and efficient method for the synthesis of structurally diversified 2-pyridones using the [4 + 2] annulation of in situ generated azadienes from N-propargylamines and active methylene compounds is demonstrated. The reaction, promoted by an inorganic base, provides moderate to good yields. The developed methodology is applicable for the direct and formal synthesis of various bioactive molecules, with the synthetic utility further illustrated by late-stage functionalization of the products.

JOURNAL OF ORGANIC CHEMISTRY (2023)

添加到收藏夹

Review Chemistry, Organic

C-H Functionalization of Aldehydes and Ketones with Transient Directing Groups: Recent Developments

Hugo Amistadi-Revol, Shanshan Liu, Sebastien Prevost

Summary: To functionalize C-H bonds of complex molecules and control the regioselectivity, various directing groups have been used. However, the installation and removal of these directing groups may limit the use of C-H activation in synthesis. A transient directing group strategy has emerged, utilizing an amine additive to achieve in situ formation of the directing group. This review presents the latest developments in this field from 2020 to 2023.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2023)

添加到收藏夹

Article Chemistry, Organic

Copper-Catalyzed Azidative Multifunctionalization of Alkynes

Guangfan Zheng, Jiaqiong Sun, Yang Liu, Shengbiao Yang, Yan Li, Haizhu Sun, Qian Zhang

JOURNAL OF ORGANIC CHEMISTRY (2017)

添加到收藏夹

Article Chemistry, Organic

Rhodium(III)-catalyzed annulative coupling between arenes and sulfoxonium ylides via C-H activation

Guangfan Zheng, Miaomiao Tian, Youwei Xu, Xiaohong Chen, Xingwei Li

ORGANIC CHEMISTRY FRONTIERS (2018)

添加到收藏夹

Article Chemistry, Multidisciplinary

Rhodium(III)-Catalyzed Enantioselective Coupling of Indoles and 7-Azabenzonorbornadienes by C-H Activation/Desymmetrization

Xifa Yang, Guangfan Zheng, Xingwei Li

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

添加到收藏夹

Article Chemistry, Organic

Rhodium(III)-Catalyzed Oxidative Allylic C-H Indolylation via Nucleophilic Cyclization

Jiaqiong Sun, Kuan Wang, Peiyuan Wang, Guangfan Zheng, Xingwei Li

ORGANIC LETTERS (2019)

添加到收藏夹

Article Chemistry, Multidisciplinary

Rhodium(III)-Catalyzed Enantio- and Diastereoselective C-H Cyclopropylation of N-Phenoxylsulfonamides: Combined Experimental and Computational Studies

Guangfan Zheng, Zhi Zhou, Guoxun Zhu, Shuailei Zhai, Huiying Xu, Xujing Duan, Wei Yi, Xingwei Li

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

添加到收藏夹

Article Environmental Sciences

Degradation mechanism study of fluoroquinolones in UV/Fe2+/peroxydisulfate by on-line mass spectrometry

Jie Jiang, Dongmei Zhang, Hong Zhang, Kai Yu, Na Li, Guangfan Zheng

CHEMOSPHERE (2020)

添加到收藏夹

Article Chemistry, Organic

Access to [4,3,1]-Bridged Carbocycles via Rhodium(III)-Catalyzed C-H Activation of 2-Arylindoles and Annulation with Quinone Monoacetals

Guangfan Zheng, Xujing Duan, Lu Chen, Jiaqiong Sun, Shuailei Zhai, Xiaojiao Li, Jierui Jing, Xingwei Li

JOURNAL OF ORGANIC CHEMISTRY (2020)

添加到收藏夹

Article Chemistry, Multidisciplinary

Synthesis of Axially Chiral Aldehydes by N-Heterocyclic-Carbene-Catalyzed Desymmetrization Followed by Kinetic Resolution

Yingtao Wu, Mingrui Li, Jiaqiong Sun, Guangfan Zheng, Qian Zhang

Summary: In this research, an NHC-catalyzed atroposelective esterification of biaryl dialdehydes is described as a general and practical strategy for the construction of axially chiral aldehydes. The method features excellent enantioselectivity, mild conditions, good functional-group tolerance, and applicability to late-stage functionalization.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2022)

添加到收藏夹

Article Chemistry, Multidisciplinary

NHC and visible light-mediated photoredox co-catalyzed 1,4-sulfonylacylation of 1,3-enynes for tetrasubstituted allenyl ketones

Lihong Wang, Ruiyang Ma, Jiaqiong Sun, Guangfan Zheng, Qian Zhang

Summary: The modulation of selectivity of highly reactive carbon radical cross-coupling for the construction of C-C bonds was achieved using N-Heterocyclic carbene (NHC) catalyzed radical transformations. This method successfully realized highly selective cross-coupling between acyl radicals and alkyl radicals for efficient construction of C-C bonds. The study further investigated the cross-coupling reaction of acyl radicals with vinyl radicals, providing valuable insights into the mechanism.

CHEMICAL SCIENCE (2022)

添加到收藏夹

Article Chemistry, Multidisciplinary

Ru anchored on Mo@MoOx nanowires as self-supported electrocatalysts for efficient hydrogen production in alkaline media

Lanlan Wang, Zhengpeng Liu, Jian Zhang

Summary: In this study, Ru-Mo@MoOx nanowires anchored on Mo@MoOx support were reported as an efficient electrocatalyst for alkaline hydrogen evolution reaction. The nanowires exhibited low overpotential and suitable Tafel slope, outperforming commercial Pt/C and most reported Ru-based electrocatalysts.

CHEMNANOMAT (2022)

添加到收藏夹

Article Chemistry, Multidisciplinary

Visible light-mediated NHCs and photoredox co-catalyzed radical 1,2-dicarbonylation of alkenes for 1,4-diketones

Lihong Wang, Jiaqiong Sun, Jiuli Xia, Mingrui Li, Lianjin Zhang, Ruiyang Ma, Guangfan Zheng, Qian Zhang

Summary: This paper presents a method for the selective 1,2-dicarbonylation of alkenes using NHCs and photocatalysis as co-catalysts, which allows for the construction of structurally diverse 1,4-diketones.

SCIENCE CHINA-CHEMISTRY (2022)

添加到收藏夹

Article Chemistry, Organic

Visible light-mediated NHC and photoredox co-catalyzed 1,2-sulfonylacylation of allenes via acyl and allyl radical cross-coupling

Lihong Wang, Jiaqiong Sun, Jiuli Xia, Ruiyang Ma, Guangfan Zheng, Qian Zhang

Summary: In this study, a novel cross-coupling reaction between an NHC-stabilized acyl radical and a delocalized allyl radical was developed, enabling the 1,2-sulfonylacylation of allenes. This methodology provides a new strategy for the synthesis of sulfonyl-containing multi-substituted allyl ketones.

ORGANIC CHEMISTRY FRONTIERS (2023)

添加到收藏夹

Article Biochemistry & Molecular Biology

Catalyst-Free Trans-Selective Oxyiodination and Oxychlorination of Alkynes Employing N-X (Halogen) Reagents

Jiaqiong Sun, Yunliang Guo, Jiuli Xia, Guangfan Zheng, Qian Zhang

Summary: In this study, versatile halogenated enol esters and ethers were directly synthesized through the facile trans-oxyiodination and oxychlorination of alkynes. This transformation offers easy operation, optimal atomic economy, strong functional group tolerance, and broad substrate scope.

MOLECULES (2023)

添加到收藏夹

Article Chemistry, Applied

Rhodium(III)-catalyzed chelation-assisted C-H imidation of arenes via umpolung of the imidating reagent

Guangfan Zheng, Jiaqiong Sun, Youwei Xu, Xukai Zhou, Hui Gao, Xingwei Li

CHINESE JOURNAL OF CATALYSIS (2020)

添加到收藏夹

暂无数据

© Peeref 2019-2024. All rights reserved.