Article
Chemistry, Multidisciplinary
Sanoop P. P. Chandrasekharan, Narendra Kumar Vaishanv, Ruchir Kant, Kishor Mohanan
Summary: A substrate-controlled reactivity switch was observed in the reaction of alpha-fluoro-beta-ketoamides with arynes. Secondary alpha-fluoro-beta-ketoamides reacted to afford alpha-aryl-alpha-fluoroacetamides through arylation/deacylation, while tertiary alpha-fluoro-beta-ketoamides underwent C-C sigma-bond insertion reaction to give 1,2-disubstituted arenes.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Multidisciplinary
Lu Han, Sheng-Jun Li, Xue-Ting Zhang, Shi-Kai Tian
Summary: The study presents an unprecedented aromatic aza-Claisen rearrangement reaction, converting arylpropargylammonium salts into 2-propargylanilines with moderate to good yields and high regioselectivity.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Applied
Wei Sang, Yan-Yan Gong, Hua Cheng, Rui Zhang, Ye Yuan, Guang-Gao Fan, Zhi-Qin Wang, Cheng Chen, Francis Verpoort
Summary: A base-controlled protocol was developed for the C-N coupling of primary amines and 2-chlorobenzimidazoles, achieving selective synthesis of secondary or tertiary amines. The selectivity can be switched from monoarylation to diarylation by changing the base from iPr(2)NH to LiOtBu. The type, intrinsic basicity, and amount of bases utilized greatly affect the reactions.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Multidisciplinary
Avishek Guin, Subrata Bhattacharjee, Akkattu T. Biju
Summary: This study demonstrates the direct C2-functionalization of pyridines through a transition-metal-free protocol using aryne multicomponent coupling. The reaction allows for the synthesis of C2-substituted pyridine derivatives bearing the -CF3 group in good yields, with activated keto esters also being employed as third components in the formal 1,2-di(hetero)arylation of ketones. Performing the reaction under dilute conditions inhibits the competing pyridine-aryne polymerization pathway, leading to the desired products.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Organic
Xian Xu, Qianlin Sun, Xin Xu
Summary: This work presents a chemo- and stereoselective benzylic C(sp(3))-H alkenylation of tertiary ortho-methyl anilines with internal alkynes using a beta-diketiminato scandium catalyst. The protocol offers an efficient method for synthesizing a new family of tertiary ortho-allylanilines in high yields, which can be further transformed into other valuable anilines. A cationic scandium benzyl species was identified as the catalytic intermediate.
Article
Biochemistry & Molecular Biology
Dmitry L. Lipilin, Alexander E. Frumkin, Alexey Y. Tyurin, Vitalij V. Levin, Alexander D. Dilman
Summary: This study describes a reaction involving aromatic halides with electron-withdrawing groups and tertiary amines in the presence of an iridium catalyst under blue light irradiation. The products obtained are the result of aromatic substitution of the halide by the dialkylamino fragment. The interaction between aryl radicals and tertiary amines to form zwitterionic radical species is believed to be the main factor contributing to the reaction efficiency.
Article
Chemistry, Organic
Qunchao Zhao, Jean M. Etersque, Shuiyu Lu, Sanjay Telu, Victor W. Pike
Summary: In this study, we investigated the use of aryliodonium precursors for copper-free labeling of PET tracers with fluorine-18. We found that regioisomeric F-18-fluoroarenes can be formed in certain labeling methods. The reaction between aryliodonium ylides derived from Meldrum's acid with para electron-donating groups and [F-18]-fluoride in acetonitrile produces regioisomeric F-18-fluoroarenes via a competing aryne pathway. The formation of regioisomers is decreased or absent in DMF. It is recommended to analytically check for the absence of the F-18-regioisomer in any specific PET tracer radiosynthesis using these or similar methods.
Article
Chemistry, Organic
Boyu Yan, Yutong Zhou, Jieliang Wu, Maogang Ran, Huihui Li, Qiuli Yao
Summary: The study presents a simple and catalyst-free photochemical strategy for the direct reduction of aryl salts and haloarenes to arenes or deuterium-labeled arenes, confirming the formation of aryl radical intermediates.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Nanoscience & Nanotechnology
Somnath Dey, Salahuddin Attar, Eric F. Manley, Salvador Moncho, Edward N. Brothers, Hassan S. Bazzi, Hugo Bronstein, Tobin J. Marks, Martin Heeney, Bob C. Schroeder, Mohammed Al-Hashimi
Summary: The novel method described in this paper utilizes a (PrMgCl)-Pr-i·LiCl complex to synthesize thiazole-based conjugated polymers without the need for a transition metal catalyst, resulting in well-defined polymers with good molecular weights. This marks the first example of fully conjugated thiazole-based aromatic homopolymers produced without the use of any transition metal catalyst.
ACS APPLIED MATERIALS & INTERFACES
(2021)
Article
Chemistry, Multidisciplinary
Yangming Ding, Tenglong Guo, Zhewei Li, Bo Zhang, Fritz E. Kuhn, Chang Liu, Jian Zhang, Dezhu Xu, Ming Lei, Tao Zhang, Changzhi Li
Summary: A one-pot cascade reaction was developed for the synthesis of quinoline from beta-O-4 model compounds, achieving high yields. The reaction pathway involves selective cleavage of C-O bonds, dehydrogenation, aldol condensation, and C-N bond formation.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Avishek Guin, Rahul N. Gaykar, Shiksha Deswal, Akkattu T. Biju
Summary: This study demonstrates a transition-metal-free, three-component, and diastereoselective [6 + 3] annulation reaction using tropone, imino esters, and arynes to synthesize bridged azabicyclo[4.3.1]decadienes. The nitrogen ylides generated from imino esters and arynes undergo regioselective addition to tropone to produce the desired products with moderate to good yields and good functional group tolerance under mild conditions.
Article
Chemistry, Multidisciplinary
Puneeth Kumar Someswara Ashwathappa, Takuya Higashi, Vincent Desrosiers, Alvaro A. Omana, Frederic-Georges Fontaine
Summary: We report a metal-free, selective Csp(3)-H borylation of saturated cyclic amines. Piperidine derivatives can be selectively borylated at either the α or β positions depending on the reaction conditions. Mechanistic studies using NMR spectroscopy, calorimetry experiments, and density functional theory computations suggest that piperidine undergoes dehydrogenation through complexation with BBr3 to generate an enamine intermediate, which is then borylated at the α or β position based on the reaction conditions.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Review
Chemistry, Organic
Mohit L. Deb, B. Shriya Saikia, Paran J. Borpatra, Pranjal K. Baruah
Summary: This review article provides an update on the metal-free photocatalyzed and photocatalyzed-free alpha-C-H functionalizations of tertiary amines promoted by visible light, discussing the current status and trends in this field.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Yifan Meng, Elumalai Gnanamani, Richard N. Zare
Summary: In this study, hydroxyl radicals generated in situ were used for an organic transformation to synthesize anilines from aryl acids and ammonia/primary or secondary amines via decarboxylation. This one-step reaction occurred at room temperature without the need for metal catalysts or organic solvents. The scope of this transformation includes various types of amines and aromatic acids, enabling the synthesis of aniline and N-substituted anilines in a single step.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Multidisciplinary
Yi-Dan Du, Bi-Hong Chen, Wei Shu
Summary: The direct and selective synthesis of primary amines from easily available precursors is challenging but important. This method utilizes ammonium carbonate as an ammonia surrogate to efficiently convert alkenes into primary amines at room temperature, providing a powerful approach for the synthesis of advanced, highly functionalized primary amines.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Review
Chemistry, Multidisciplinary
Tony Roy, Akkattu T. Biju
CHEMICAL COMMUNICATIONS
(2018)
Article
Chemistry, Organic
Fabien Gelat, Thomas Poisson, Akkattu T. Biju, Xavier Pannecoucke, Tatiana Besset
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2018)
Article
Chemistry, Organic
Rahul N. Gaykar, Anup Bhunia, Akkattu T. Biju
JOURNAL OF ORGANIC CHEMISTRY
(2018)
Article
Chemistry, Organic
Subrata Mukherjee, Arghya Ghosh, Udaya Kiran Marelli, Akkattu T. Biju
Article
Chemistry, Organic
Atanu Patra, Fabien Gelat, Xavier Pannecoucke, Thomas Poisson, Tatiana Besset, Akkattu T. Biju
Article
Chemistry, Organic
Fabien Gelat, Atanu Patra, Xavier Pannecoucke, Akkattu T. Biju, Thomas Poisson, Tatiana Besset
Review
Chemistry, Multidisciplinary
Subrata Mukherjee, Akkattu T. Biju
CHEMISTRY-AN ASIAN JOURNAL
(2018)
Review
Chemistry, Multidisciplinary
Santigopal Mondal, Santhivardhana Reddy Yetra, Subrata Mukherjee, Akkattu T. Biju
ACCOUNTS OF CHEMICAL RESEARCH
(2019)
Article
Chemistry, Organic
Arghya Ghosh, Atanu Patra, Subrata Mukherjee, Akkattu T. Biju
JOURNAL OF ORGANIC CHEMISTRY
(2019)
Article
Chemistry, Organic
Rahul N. Gaykar, Subrata Bhattacharjee, Akkattu T. Biju
Article
Chemistry, Physical
Tamal Kanti Das, Avik Ghosh, Kuruva Balanna, Pradipta Behera, Rajesh G. Gonnade, Udaya Kiran Marelli, Abhijit Kumar Das, Akkattu T. Biju
Article
Chemistry, Organic
Subrata Bhattacharjee, Avishek Guin, Rahul N. Gaykar, Akkattu T. Biju
Article
Polymer Science
David M. Guptill, Bhavani Shankar Chinta, Trinadh Kaicharla, Shu Xu, Thomas R. Hoye
Summary: Poly(ester-amide)s (PEAs) were prepared by reacting MVL-derived diamidodiols with diacid chlorides in solution, resulting in materials with plastic properties. The stiffness of the materials can be tuned by choosing appropriate precursors. NMR studies were used to detect the degradation products of these materials.
Article
Chemistry, Multidisciplinary
Trinadh Kaicharla, Birte M. Zimmermann, Martin Oestreich, Johannes F. Teichert
CHEMICAL COMMUNICATIONS
(2019)
Article
Chemistry, Multidisciplinary
Tony Roy, Rahul N. Gaykar, Subrata Bhattacharjee, Akkattu T. Biju
CHEMICAL COMMUNICATIONS
(2019)
