☆ 4.4 Article

TsNBr2 promoted decarboxylative bromination of α,β-unsaturated carboxylic acids

TETRAHEDRON LETTERS (2018)

期刊

TETRAHEDRON LETTERS

卷 59, 期 52, 页码 4593-4596

出版社

PERGAMON-ELSEVIER SCIENCE LTD

DOI: 10.1016/j.tetlet.2018.11.041

关键词

Decarboxylative bromination; TsNBr2; beta-Bromostyrene; 1-Bromoalkyne; Cinnamic acid; Propiolic acid

类别

Chemistry, Organic

资金

SERB, India [EMR/2016/007883]
UGC, India

向作者/读者索取更多资源

Protocol

Reagent

摘要

A rapid process for decarboxylative bromination of alpha,beta-unsaturated carboxylic acids have been developed using N,N-dibromo-p-toluenesulfonamide (TsNBr2). Treatment of cinnamic acids with TsNBr2 in presence of potassium carbonate in acetonitrile produces corresponding beta-bromostyrenes at room temperature. Exclusive formation of (E)-beta-bromostyrenes was observed in a stereoselective manner within a very short period of time (5-15 min). This method was further extended for obtaining 1-bromoalkynes from corresponding propiolic acids. Instantaneous formation of bromoalkynes was observed when the reaction was carried out in presence of DBU as a base in acetonitrile at room temperature. A wide variety of cinnamic acids and propiolic acids could be converted to corresponding beta-bromostyrenes and 1-bromoalkynes respectively under mild reaction condition with high to excellent yield. (C) 2018 Elsevier Ltd. All rights reserved.

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

4.4

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

Iron-photocatalyzed double decarboxylative coupling reactions of alkynoic acids and alkyl carboxylic acids: access to alkylated alkynes

Hyemin Kang, Seunghwan An, Sunwoo Lee

Summary: An efficient iron-photocatalyzed approach was developed for the double decarboxylative coupling of alkynoic acids and alkyl carboxylic acids, providing easy access to alkylated alkynes. The Fe(NO3)3 & BULL;9H2O or FeCl2/TPA catalyst exhibited good activity under blue light conditions in the presence of PhI(OAc)2, showing good functional-group tolerance and activity towards primary, secondary, and tertiary alkyl carboxylic acids. Under the iron-photocatalytic system, the double decarboxylative coupling of alkynoic acids and alkyl carboxylic acids yielded alkylated alkynes in good yields.

ORGANIC CHEMISTRY FRONTIERS (2023)

添加到收藏夹

Article Chemistry, Organic

Microwave-Assisted Cu(I)-Catalyzed Synthesis of Unsymmetrical 1,4-Diamino-2-butynes via Cross-A3-Coupling/Decarboxylative A3-Coupling

Xianjun Xu, Huangdi Feng, Erik V. Van der Eycken

Summary: An efficient synthesis route for unsymmetric 1,4-diamino-2-butynes has been developed using a microwave-assisted Cu(I)-catalyzed cross-A(3)-coupling/decarboxylative coupling process. The multicomponent reaction yields target products in moderate to good yields with high chemoselectivity.

JOURNAL OF ORGANIC CHEMISTRY (2021)

添加到收藏夹

Article Chemistry, Multidisciplinary

Copper-catalyzed decarboxylative Se insertion coupling of indoles and propiolic acids

Ge Wu, Xueying Zhou, Caihong Wang

Summary: A novel and efficient method for decarboxylative alkynylselenation of indoles using Se powder and propiolic acids as catalyst has been developed. This method avoids the use of prefabricated arylselenation reagent and over-seleniumation issues and enriches the chemistry of selenium powder. Furthermore, this reaction can be extended to pyrrole, and its practical utility has been demonstrated in gram-scale synthesis and late-stage indolylselenation of Clofibrate-derived propiolic acid.

CHINESE CHEMICAL LETTERS (2022)

添加到收藏夹

Article Chemistry, Organic

Paired electrolysis enables decarboxylative coupling of alkenyl acids with diazo compounds

Jingchao Jiao, Yapeng Yan, Qiumin Ke, Yusen Zhang, Hang Huang, Qianwen Gao, Jie Liu, Xi Wang

Summary: Here, an efficient and green paired electrolysis strategy for decarboxylative coupling of alkenyl acids with diazo compounds is reported, providing a wide range of beta,gamma-alkenyl esters and amides. The method exhibits high stereoselectivity and avoids the use of transition metals and chemical redox regents. Additionally, the protocol allows for the easy synthesis of dideuterated products with a high deuterium incorporation level (93-99% D-inc.) by directly utilizing D2O, highlighting its significant value.

ORGANIC CHEMISTRY FRONTIERS (2023)

添加到收藏夹

Article Chemistry, Organic

Copper-Catalyzed Aerobic Oxidative/Decarboxylative Phosphorylation of Aryl Acrylic Acids with P(III)-Nucleophiles

Biquan Xiong, Lulu Si, Longzhi Zhu, Yu Liu, Weifeng Xu, Ke-Wen Tang, Shuang-Feng Yin, Peng-Cheng Qian, Wai-Yeung Wong

Summary: A copper-catalyzed aerobic oxidative/decarboxylative phosphorylation of aryl acrylic acids with P(III)-nucleophiles via the Michaelis-Arbuzov rearrangement is reported. The reaction can be carried out effectively without the use of a ligand and a base. Various aryl acrylic acids and P(III)-nucleophiles are compatible in this transformation, providing β-keto-organophosphorus compounds with good to excellent yields. The possible mechanism and kinetic studies show that this transformation may proceed through second-order chemical kinetics and involves a radical process.

JOURNAL OF ORGANIC CHEMISTRY (2023)

添加到收藏夹

Article Chemistry, Multidisciplinary

Palladium-Catalyzed Decarboxylative Homodimerization of Propiolic Acids: Synthesis of 1,3-Enynes

Eunkyeong Seo, Jonghoon Oh, Sunwoo Lee

Summary: This study showed that aryl propiolic acids with electron-donating substituents were able to undergo decarboxylative homodimerization reaction to produce the desired product, while those with electron-withdrawing substituents did not yield the desired product.

BULLETIN OF THE KOREAN CHEMICAL SOCIETY (2021)

添加到收藏夹

Review Chemistry, Organic

Microwave-assisted decarboxylative reactions: advanced strategies for sustainable organic synthesis

Qingqing You, Mingjie Liao, Huangdi Feng, Junhai Huang

Summary: The decarboxylation or decarboxylative coupling reactions of carboxylic acids and their derivatives are essential tools for organic synthesis. Microwave-assisted technology, recognized by both industry and academia, has been employed for sustainable organic synthesis. This review focuses on the recent developments in microwave-assisted decarboxylative reactions, including transition-metal-catalyzed and metal-free approaches.

ORGANIC & BIOMOLECULAR CHEMISTRY (2022)

添加到收藏夹

Article Chemistry, Multidisciplinary

A Unified Approach to Decarboxylative Halogenation of (Hetero)aryl Carboxylic Acids

Tiffany Q. Chen, P. Scott Pedersen, Nathan W. Dow, Remi Fayad, Cory E. Hauke, Michael C. Rosko, Evgeny O. Danilov, David C. Blakemore, Anne-Marie Dechert-Schmitt, Thomas Knauber, Felix N. Castellano, David W. C. MacMillan

Summary: In this study, a general catalytic method for direct decarboxylative halogenation of (hetero)aryl carboxylic acids was reported, accommodating an exceptionally broad scope of substrates. The research leveraged an aryl radical intermediate towards two divergent functionalization pathways.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2022)

添加到收藏夹

Article Plant Sciences

Cinnamomum verum extract inhibits NOX2/ROS and PKCδ/JNK/AP-1/NF-κB pathway-mediated inflammatory response in PMA-stimulated THP-1 monocytes

Na-Yeon Kim, Seonhwa Kim, Hyo-Min Park, Chae-Min Lim, Jinju Kim, Jae-Young Park, Kyeong-Bae Jeon, Amrit Poudel, Hee Pom Lee, Sei-Ryang Oh, Jongmin Ahn, Do-Young Yoon

Summary: This study found that Cinnamomum verum has anti-inflammatory and antioxidant effects in PMA-stimulated THP-1 cells. C. verum and its components, cinnamic acid and coumarin, significantly reduced the expression of IL-1 beta, IL-8, CCL5, and COX-2 in PMA-stimulated THP-1 cells. It also decreased ROS levels via NOX2 downregulation and inhibited the activation of PKC delta/JNK/AP-1/NF-kappa B signaling pathway.

PHYTOMEDICINE (2023)

添加到收藏夹

Article Biochemistry & Molecular Biology

Development of an enzyme-enhancer system to improve laccase biological activities

Somayeh Mojtabavi, Mohammad Reza Khoshayand, Mohammad Reza Fazeli, Mohammad Ali Faramarzi, Nasrin Samadi

Summary: The in-vitro study using a combination of laccase and cinnamic acid showed significant inhibition of pathogenic microorganisms growth and biofilm formation, as well as teeth whitening effects. The combination also successfully removed teeth discoloration caused by coffee without causing surface damage. The study further demonstrated the redox potential values of phenolic monomers/oligomers are related to their biological activities.

INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES (2021)

添加到收藏夹

Article Chemistry, Organic

Copper-Catalyzed Decarboxylative Elimination of Carboxylic Acids to Styrenes

Michael P. Stanton, Jessica M. Hoover

Summary: A copper-catalyzed decarboxylative elimination reaction of (hetero)aromatic propionic acids to vinyl (hetero)arenes has been developed. This method provides alkenes from carboxylic acids without the need for stoichiometric Pb or Ag additives or expensive or specialized photocatalysts. Mechanistic experiments show that the reaction proceeds via benzylic deprotonation and subsequent radical decarboxylation, which is different from the single electron-transfer mechanisms in related reactions.

JOURNAL OF ORGANIC CHEMISTRY (2023)

添加到收藏夹

Article Multidisciplinary Sciences

Ni-electrocatalytic Csp3-Csp3 doubly decarboxylative coupling

Benxiang Zhang, Yang Gao, Yuta Hioki, Martins S. Oderinde, Jennifer X. Qiao, Kevin X. Rodriguez, Hai-Jun Zhang, Yu Kawamata, Phil S. Baran

Summary: “Cross-coupling reactions are powerful tools for rapidly assembling complex molecules, but their use is limited by traditional oxidative electrolytic protocols. This study demonstrates a mildly reductive Ni-electrocatalytic system that enables coupling of different carboxylates through in situ generation of redox-active esters. This simple and versatile method offers a powerful new approach for synthesis by heterocoupling various levels of redox-active esters.”

NATURE (2022)

添加到收藏夹

Review Chemistry, Medicinal

A review on ferulic acid and analogs based scaffolds for the management of Alzheimer's disease

Yash Pal Singh, Himanshu Rai, Gourav Singh, Gireesh Kumar Singh, Sunil Mishra, Saroj Kumar, S. Srikrishna, Gyan Modi

Summary: Alzheimer's disease is an age-related neurodegenerative disorder characterized by central cholinergic neuronal loss leading to cognitive dysfunction and impaired motor activity. Current therapies only offer symptomatic relief without addressing the underlying factors, and there is no drug to slow down disease progression. Researchers are investigating new hybrid compounds, such as ferulic acid-based derivatives, as potential treatments for Alzheimer's disease.

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY (2021)

添加到收藏夹

Article Biochemistry & Molecular Biology

Design, synthesis of Cinnamyl-paeonol derivatives with 1, 3-Dioxypropyl as link arm and screening of tyrosinase inhibition activity in vitro

Kai Tang, Yi Jiang, Huawei Zhang, Wenli Huang, Yundong Xie, Chong Deng, Hongbo Xu, Xiaomei Song, Hong Xu

Summary: This study synthesized a series of cinnamyl ester analogues, with compound 13 showing strong tyrosinase inhibitory activity and anti-melanogenesis effects, making it a potential candidate for novel tyrosinase inhibitors and whitening agents.

BIOORGANIC CHEMISTRY (2021)

添加到收藏夹

Review Biochemistry & Molecular Biology

Hybrids as NO Donors

Ioanna-Chrysoula Tsopka, Dimitra Hadjipavlou-Litina

Summary: Cinnamic acid and its derivatives have been studied for their various biological properties such as anti-inflammatory, antioxidant, anticancer, antihypertensive, and antibacterial effects. Hybrids of cinnamic derivatives with other bioactive molecules have been synthesized and evaluated as nitric oxide (NO) donors, incorporating NO donor groups to enhance their biological properties for the treatment of several diseases.

INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES (2021)

添加到收藏夹

Article Chemistry, Multidisciplinary

Metal-Free One-Pot Conversion of Olefins and Alkynes to Amides Using TsNBr2, I2 and Aqueous NH3 at Room Temperature

Dineshwori Chanu Loukrakpam, Prodeep Phukan

CHEMISTRYSELECT (2019)

添加到收藏夹

Article Chemistry, Multidisciplinary

Accelerating Effect of DMAP on CuI Catalyzed Buchwald-Hartwig C-N Coupling: Mechanistic Insight to the Reaction Pathway

Subhasish Roy, Mintu Maan Dutta, Manas Jyoti Sarma, Prodeep Phukan

CHEMISTRYSELECT (2019)

添加到收藏夹

Article Chemistry, Organic

A Unified Approach for the Synthesis of Isourea and Isothiourea from Isonitrile and N,N-Dibromoarylsulfonamides

Debashish Mishra, Prodeep Phukan

Summary: A unified approach has been developed for the synthesis of both isourea and isothiourea in a three-component coupling reaction, yielding a library of sulfonylisoureas and isothioureas with wide substrate scope and good to high yields.

JOURNAL OF ORGANIC CHEMISTRY (2021)

添加到收藏夹

Article Biochemistry & Molecular Biology

Silver acetate-catalyzed synthesis of cyclic sulfonyl guanidine with exocyclic double bond

Dikshita Goswami, Debashish Mishra, Prodeep Phukan

Summary: An efficient protocol for synthesizing cyclic guanidine with an exocyclic double bond has been developed, demonstrating short reaction time, wide substrate scope, and good functional group tolerance.

MOLECULAR DIVERSITY (2023)

添加到收藏夹

Article Chemistry, Multidisciplinary

A Switchable Protocol for Selective Synthesis of gem-Dibromo Compounds and Amides from Ketoximes using TsNBr2

Debashish Mishra, Dineshwori Chanu Loukrakpam, Smriti Rekha Neog, Debojit Hazarika, Prodeep Phukan

Summary: A metal-free method has been developed for the selective synthesis of N-substituted amide and alpha,alpha-dibromoketones. The product selectivity can be switched by adding or excluding a base. Additionally, a novel strategy has been developed for the synthesis of 1-(dibromomethyl)benzenes directly from aldehydes under metal-free conditions.

CHEMISTRYSELECT (2022)

添加到收藏夹

Article Chemistry, Organic

Cascade Synthesis of 5-Aminotetrazoles from Isonitriles and N,N-Dibromoarylsulfonamides via Carbodiimide Coupling with Azide

Debashish Mishra, Sauvik Kashyap, Prodeep Phukan

Summary: A cascade protocol for the synthesis of aminotetrazoles has been developed, achieving excellent yields and broad substrate scope without the use of any metals. The reaction proceeds via an isolable carbodiimide intermediate and intermolecular cyclization, providing 5-aminotetrazoles in a short reaction time.

JOURNAL OF ORGANIC CHEMISTRY (2023)

添加到收藏夹

Article Chemistry, Organic

Bromamine-T (TsNBrNa): A Biologically Significant, Versatile Bromo-Organic Reagent

Sauvik Kashyap, Prodeep Phukan

Summary: Bromamine-T is an organic haloamine compound that acts as an oxidizing agent and displays basic and nucleophilic properties. It is widely used as an efficient reagent for various organic transformations due to its low toxicity and mild reaction conditions, making it of great interest to researchers.

SYNLETT (2023)

添加到收藏夹

Article Chemistry, Multidisciplinary

bis-(Aminophenyl)ferrocene ligand for palladium free CuI catalyzed Csp2-Csp cross-coupling reaction

Bishwapran Kashyap, Hrishikesh Talukdar, Prodeep Phukan

Summary: Two new ferrocene based molecules were synthesized and applied as ligands for catalytic coupling reactions. These ligands demonstrated high efficiency in coupling reactions between alkynes and aromatic compounds.

CHEMISTRYSELECT (2023)

添加到收藏夹

Article Chemistry, Multidisciplinary

Nucleophilicity and CO2 fixation ability of phosphorus, nitrogen and sulfur ylides: insights on stereoelectronic factors from DFT study

Dipanjali Pathak, Sanjib Deuri, Prodeep Phukan

Summary: The nucleophilicity and CO2 fixation ability of ylides of phosphorous, sulfur, and nitrogen were assessed using DFT calculations, showing a linear correlation between binding energy of the CO2 adducts and nucleophilicity.

JOURNAL OF CHEMICAL SCIENCES (2021)

添加到收藏夹

Article Chemistry, Multidisciplinary

Catalytic activity of a microporous-mesoporous composite towards liquid phase oxidation of diphenylmethane

Priyanka Kalita, Doli Rani Das, Debojit Hazarika, Anup Kumar Talukdar

Summary: A ZSM-5/MCM-41 composite was synthesized using pre-synthesized ZSM-5 zeolite as a silica source and CTAB as a template, followed by in-situ modification to load varying amounts of cobalt. Characterization techniques such as PXRD, FT-IR, TGA, UV-Vis DRS, N-2 adsorption-desorption, and SEM-EDX were used to analyze the materials. The catalytic activity of the materials for liquid phase oxidation of diphenylmethane was studied, with a focus on enhancing selectivity towards benzophenone.

NEW JOURNAL OF CHEMISTRY (2021)

添加到收藏夹

Article Chemistry, Multidisciplinary

Unprecedented 1,3-tert-butyl migration via the C-N single bond scission of isonitrile: an expedient metal-free route to N-sulfonyl amidines

Debashish Mishra, Arun Jyoti Borah, Pinakinee Phukan, Debojit Hazarika, Prodeep Phukan

CHEMICAL COMMUNICATIONS (2020)

添加到收藏夹

Article Chemistry, Inorganic & Nuclear

CuI incorporated cobalt ferrite nanoparticles as a magnetically separable catalyst for oxidative amidation reaction

Mintu Maan Dutta, Hrishikesh Talukdar, Prodeep Phukan

DALTON TRANSACTIONS (2019)

添加到收藏夹

Article Chemistry, Multidisciplinary

Facile, catalyst-free cascade synthesis of sulfonyl guanidines via carbodiimide coupling with amines

Debojit Hazarika, Arun Jyoti Borah, Prodeep Phukan

CHEMICAL COMMUNICATIONS (2019)

添加到收藏夹

Article Chemistry, Organic

Pyrrolidine-based C1-symmetric chiral transition metal complexes as catalysts in the asymmetric organic transformations

Geeta Devi Yadav, Pooja Chaudhary, Balaram Pani, Surendra Singh

Summary: Chiral transition metal complexes with privileged ligands are efficient catalysts for various asymmetric organic transformations. Transition metal complexes of C1-symmetric pyrrolidine-based ligands have been widely used in asymmetric organic reactions. However, a comprehensive review article on the transition metal complexes of chiral C1-symmetric pyrrolidine-based ligands derived from (L)-proline has not been published.

TETRAHEDRON LETTERS (2024)

添加到收藏夹

© Peeref 2019-2024. All rights reserved.