Article
Chemistry, Multidisciplinary
Zhiyuan Bao, Chao Chen
Summary: An efficient method for the synthesis of multi-substituted cyclic imides was developed using cyanoesters and diaryliodonium salts. This method involves a cascade of N-arylation-acylation and rearrangement reactions, producing the desired heterocycles in high yields. The method has a broad substrate scope, excellent functional group compatibility, and can be extended to fused cyclic imides.
CHINESE CHEMICAL LETTERS
(2023)
Article
Chemistry, Organic
Hui Peng, Qian Liu, Yameng Sun, Bingling Luo, Tianyian Yu, Peng Huang, Daqian Zhu, Shijun Wen
Summary: In this study, it was demonstrated that linear unsymmetrical diaryliodoniums can undergo one-pot cyclization/arylation using a dual nickel/palladium metal system, and the in situ generated benzoxazole motifs can be utilized as directing groups for subsequent C-H activated arylation from the unwanted aryl iodide, exhibiting good atom economy and regioselectivity.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Multidisciplinary
Shubhendu S. Karandikar, Avik Bhattacharjee, Bryan E. Metze, Nicole Javaly, Edward J. Valente, Theresa M. McCormick, David R. Stuart
Summary: Diarylhalonium compounds play important roles as reagents and catalysts in organic synthesis, with the key reactivity of the three center, four electron bond requiring refinement for broader applicability. The combination of Density Functional Theory, Natural Bond Orbital Theory, and X-ray structure data can provide insights into the bonding and structure of these compounds.
Article
Chemistry, Organic
Aleksandra Nilova, Bryan Metze, David R. Stuart
Summary: Controlling reaction pathways selectively leads to a broad scope of arenes and arynophiles, offering efficient access to diverse arene chemical space and biologically active compounds with high yields.
Review
Chemistry, Medicinal
Thierry Besson, Corinne Fruit
Summary: This review highlights recent synthetic advances in the late-stage C(sp2)-N and C(sp2)-C(sp2) bond-forming reactions under metal-free conditions using diaryliodonium salts as arylating reagents, and discusses their applications in the synthesis of new arylated bioactive heterocyclic compounds.
Article
Chemistry, Multidisciplinary
Gabriella Kervefors, Leonard Kersting, Berit Olofsson
Summary: A transition metal-free approach using unsymmetric diaryliodonium salts with anisyl ligands has been developed for the N-arylation of amino acid derivatives, achieving high chemoselectivity and yields. This method is applicable for transferring electron deficient, electron rich, and sterically hindered aryl groups, and a cyclic diaryliodonium salt was successfully employed. The N-arylated products were obtained with retained enantiomeric excess.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Multidisciplinary
Erika Linde, David Bulfield, Gabriella Kervefors, Nibadita Purkait, Berit Olofsson
Summary: This study combines nucleophilic aromatic substitution and hypervalent iodine-mediated arylations to achieve a transition-metal-free difunctionalization of N and O-nucleophiles, providing di-and triarylamines and diaryl ethers in one single step. The unique reactivity discovered with specifically designed fluorinated diaryliodonium salts unveils novel reaction pathways in hypervalent iodine chemistry. The methodology tolerates a wide variety of functional and protecting groups, allowing for easy derivatization of the products.
Review
Chemistry, Multidisciplinary
Cheng Pan, Limin Wang, Jianwei Han
Summary: This account summarizes our research interest in synthetic methodology with diaryliodonium salts. In addition to employing a dual activation strategy of C-I and ortho C-H bonds, we have introduced vicinal functional groups at the ortho-positions of diaryliodonium salts and explored their unique reactivities in various processes, including arylation, diarylation, cascade annulation, benzocyclization, arylocyclization, and intramolecular aryl migration. The diverse mechanisms of these reactions involving transition metals, especially palladium in organometallic catalysis, or transition-metal free conditions, are discussed in the context.
Article
Chemistry, Physical
Alexandra Pacheco-Benichou, Eugenie Ivendengani, Ioannis K. Kostakis, Thierry Besson, Corinne Fruit
Summary: The copper-catalyzed Csp2-Csp2 bond forming reactions through C-H activation offer a useful strategy for the diversification of heterocyclic moieties. Specific phenylation of fused-pyrimidinones, including quinazolinone, has been achieved using this method, leading to the rapid access of various arylated N-containing polyheteroaromatics as potential bioactive compounds.
Article
Chemistry, Inorganic & Nuclear
Allan J. Canty, Alireza Ariafard, Helena C. Matinakova
Summary: The study uses Density Functional Theory to examine the synthesis of benzofurans through the reaction of a palladium complex with hypervalent iodine(III) reagents. It reveals the key role of oxidative alkenylation, initial adduct formation, and 'chain-walking' at Pd-II centers in the annulation process. Computational analysis helps to reinterpret NMR data and determine barriers in the reaction pathway for key intermediates.
DALTON TRANSACTIONS
(2022)
Article
Chemistry, Multidisciplinary
Argha Saha, Srimanta Guin, Wajid Ali, Trisha Bhattacharya, Sheuli Sasmal, Nupur Goswami, Gaurav Prakash, Soumya Kumar Sinha, Hediyala B. Chandrashekar, Sanjib Panda, S. S. Anjana, Debabrata Maiti
Summary: The Fujiwara-Moritani reaction has made a significant contribution to contemporary C-H activation protocols. By establishing a photoredox catalytic system, the regioselective Fujiwara-Moritani reaction can be achieved through visible light without the need for silver salts and thermal energy. This sustainable protocol has importance in synthesizing natural products, chiral molecules, drugs, and diversifying functionalizations.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Multidisciplinary
Avery J. To, Graham K. Murphy
Summary: In this study, it was discovered that cyclic diaryliodonium salts can act as effective Lewis-acidic halogen-bond donor catalysts in the Nazarov cyclization reaction.
NEW JOURNAL OF CHEMISTRY
(2022)
Article
Multidisciplinary Sciences
Jae Bin Lee, Gun Ha Kim, Ji Hwan Jeon, Seo Yeong Jeong, Soochan Lee, Jaehyun Park, Doyoung Lee, Youngkook Kwon, Jeong Kon Seo, Joong-Hyun Chun, Seok Ju Kang, Wonyoung Choe, Jan-Uwe Rohde, Sung You Hong
Summary: The authors present a transition-metal-free, radical relay pi-extension approach to produce N-doped polycyclic aromatic compounds directly from simple azines and cyclic iodonium salts. This method offers a solution to the limitation of low reactivity in unactivated azines.
NATURE COMMUNICATIONS
(2022)
Article
Chemistry, Organic
Yohann Landrain, Gwilherm Evano
Summary: An efficient copper-catalyzed inter/intramolecular oxy/aminoarylation of gamma-hydroxy/aminoalkenes with diaryliodonium triflates is described. Activation of the arylating agents and the alkene with copper(II) triflate in dichloromethane leads to the formation of highly substituted tetrahydrofurans and pyrrolidines, depending on the nature of the internal nucleophile. The cyclization process is stereospecific and can also be extended to oxyalkynylation.
Article
Chemistry, Organic
Bangxiong Kang, Lu Wang, Xihu Sun, Hongjian Liu, Zhonglin Wen, Yanwei Ren, Chaorong Qi, Huanfeng Jiang
Summary: This study reports a copper-catalyzed ring opening reaction of carbon dioxide (CO2) with amines, leading to the synthesis of a range of axially chiral carbamates. The method offers mild conditions, broad substrate scope, and excellent enantioselectivity. The synthetic applications of the method were demonstrated through the modification of natural products and drug molecules, as well as the diverse transformations of the axially chiral products.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Dipak D. Vachhani, Amit Kumar, Sachin G. Modha, Sunil K. Sharma, Virinder S. Parmar, Erik V. Van der Eycken
SYNTHESIS-STUTTGART
(2015)
Article
Chemistry, Organic
Sachin G. Modha, Mihai V. Popescu, Michael F. Greaney
JOURNAL OF ORGANIC CHEMISTRY
(2017)
Article
Chemistry, Organic
Amit Kumar, Dipak D. Vachhani, Sachin G. Modha, Sunil K. Sharma, Virinder S. Parmar, Erik V. Van der Eycken
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
(2013)
Review
Chemistry, Multidisciplinary
Sachin G. Modha, Vaibhav P. Mehta, Erik V. Van der Eycken
CHEMICAL SOCIETY REVIEWS
(2013)
Article
Chemistry, Organic
Nigam M. Mishra, Dipak D. Vachhani, Sachin G. Modha, Erik V. Van der Eycken
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2013)
Article
Chemistry, Organic
Dipak D. Vachhani, Amit Kumar, Sachin G. Modha, Sunil K. Sharma, Virinder S. Parmar, Erik V. Van der Eycken
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2013)
Article
Chemistry, Organic
Amit Kumar, Dipak D. Vachhani, Sachin G. Modha, Sunil K. Sharma, Virinder S. Parmar, Erik V. Van der Eycken
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2013)
Article
Chemistry, Organic
Amit Kumar, Dipak D. Vachhani, Sachin G. Modha, Sunil K. Sharma, Virinder S. Parmar, Erik V. Van der Eycken
SYNTHESIS-STUTTGART
(2013)
Article
Chemistry, Organic
Dipak D. Vachhani, Sachin G. Modha, Abhishek Sharma, Erik V. Van der Eycken
Article
Chemistry, Organic
Sachin G. Modha, Alexander Poethig, Andreas Dreuw, Thorsten Bach
JOURNAL OF ORGANIC CHEMISTRY
(2019)
Review
Chemistry, Multidisciplinary
Rinkal B. Bhoraniya, Sachin G. Modha
Summary: The Ugi reaction is a multicomponent reaction that enables diversity-oriented synthesis. Its significance is well-recognized due to the growing number of publications utilizing post-Ugi transformations as a simple and sustainable strategy to construct complex molecules. Alkyne activation through metal-, acid-, iodine-catalysis, and base-mediated transformations also lead to efficient synthesis of wonderful molecules. Combining these two approaches by employing an alkyne-containing component in the Ugi reaction allows the benefits of both protocols to be integrated into one synthetic sequence. This review focuses on the application of propargyl amines in the Ugi reaction, particularly in post-Ugi transformations.
Article
Chemistry, Organic
Rinkal B. Bhoraniya, Mahesh Koladiya, Shiv R. Desai, Sachin G. Modha
Summary: A Biginelli, hydrolysis and Ugi four-component reaction sequence was developed to synthesize novel dihydropyrimidinone (DHPM) bisamides. An unprecedented but moderate 1,6 asymmetric induction was observed for this compound class. A detailed study was carried out to investigate the effects of various substitutions on the diastereoselectivity. The results showed that steric congestion caused sluggish Mumm rearrangement, leading to the formation of side products by trapping the imidate intermediate with methanol.
Editorial Material
Chemistry, Organic
Sachinkumar G. Modha
SYNTHESIS-STUTTGART
(2020)
Article
Chemistry, Multidisciplinary
Christopher J. Teskey, Shariar M. A. Sohel, Danielle L. Bunting, Sachin G. Modha, Michael F. Greaney
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2017)