Article
Chemistry, Organic
Hongpeng Bao, Yongjin Guo, Jiarong Shi, Yang Li
Summary: Two sets of cascade processes were achieved by benzyne insertion into the Se=O bond. The differential factors in these processes are the structures of diaryl selenium oxides and reaction conditions. When diaryl selenium oxides with an ortho weak Sigma- electron-withdrawing group were used, triarylselenonium salts were obtained at room temperature, while ortho-(aryloxy)phenyl phenyl selanes could be produced from diaryl selenium oxides at 100 degrees C.
Article
Multidisciplinary Sciences
Shuai Liu, Xu Cheng
Summary: The authors demonstrate a novel methodology for the synthesis of aromatic heterocycles containing nitrogen by electrochemically inserting nitrogen atoms into a carbon ring using ammonia. This approach offers high atom and step economy, making it valuable for extensive applications in chemical and biological research, with significant potential for drug development.
NATURE COMMUNICATIONS
(2022)
Article
Chemistry, Organic
Yongjin Guo, Hongpeng Bao, Liyuan Chen, Jiarong Shi, Yang Li
Summary: An insertion reaction of benzyne into the Se=O bond has been successfully achieved, leading to the synthesis of two different types of selenium-containing compounds from various substrates.
Article
Chemistry, Organic
Justin S. Lamb, Futa Koyama, Noriyuki Suzuki, Yumiko Suzuki
Summary: Carbon atom insertion into a cyclic framework is an attractive method for molecular editing, allowing modification of the core skeleton and controlled increases in size and complexity. Through experiments, it was discovered that a reaction between benzimidazoliums and 2-(methylsulfonyl)chromones under specific conditions resulted in the insertion of a carbon atom, forming biologically active compounds.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Multidisciplinary
Eva Kran, Christian Muck-Lichtenfeld, Constantin G. Daniliuc, Armido Studer
Summary: In this study, the reaction of in situ generated arynes with stannylated imines to provide ortho-stannyl-aniline derivatives was reported, with good yields and regioselectivities. The product anilines are valuable starting materials for follow-up chemistry due to the rich chemistry offered by the trimethylstannyl moiety.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Multidisciplinary
Wen-Xuan Cao, Lei Zhu, Yiyi He, Run Wang, Ming Liu, Qin Ouyang, Qing Xiao
Summary: The first aryne insertions into the carbon-iodine bond of heteroaryl iodides have been achieved. This novel reaction provides an efficient pathway for the synthesis of valuable building blocks 2-iodoheterobiaryls with excellent regioselectivity by reacting heteroaryl iodides and o-silylaryl triflates. The copper(I) catalyst, which contains a N-heterocyclic carbene (NHC) ligand, is essential for the reaction. Control reactions and DFT calculations suggest that the coordination of copper, acting as a Lewis acid, with nitrogen atoms of heteroaryl iodides mediates the aryne insertions into heteroaryl carbon-iodine bonds.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Inorganic & Nuclear
Jianwei Jiang, Sohee Choi, Jaehyun Oh, Jihyun Choi, Ho-Jung Sun, Sungho Yoon
Summary: This article introduces a nonclassical and highly effective method for synthesizing mononuclear N,O-chelate zirconium complexes, which utilizes the ring-opening insertion of epoxide into zirconium complexes at room temperature. Experimental results demonstrate that the produced precursor complex enables satisfactory growth rate of ZrO2 in ALD.
DALTON TRANSACTIONS
(2022)
Article
Chemistry, Organic
Jinglan Lei, Min Li, Qingqing Zhang, Shuyang Liu, Haifang Li, Lei Shi, Wen-Feng Jiang, Chunying Duan, Yunhe Jin
Summary: We report a convenient and manipulable synthesis of methylenebisamide derivatives through visible-light-driven radical cascade reactions incorporating C(sp3)-H activation and C-N/ N-O cleavage. Mechanistic studies reveal the involvement of both a traditional Ir-catalyzed photoredox pathway and a novel copper-induced complex-photolysis pathway, enabling the activation of inert N-methoxyamides and the synthesis of valuable bisamides. This approach offers many advantages, including mild reaction conditions, broad scope and functional group tolerance, and competitive step economy. With its mechanistic plenitude and operational simplicity, we believe this method paves a promising way for the synthesis of valuable nitrogen-containing molecules.
Article
Chemistry, Multidisciplinary
Hang Li, Na Li, Jinghao Wu, Tianyang Yu, Ran Zhang, Li-Ping Xu, Hao Wei
Summary: In this study, a method for direct insertion of an intramolecular nitrogen atom into an aromatic C-C bond was described. Carbamoyl azides were activated by a Rh catalyst and inserted directly into the C-C bond of an arene ring to produce fused azepine products. The use of a paddlewheel dirhodium complex effectively inhibited the undesired C-H insertion. Density functional theory calculations were used to elucidate the reaction mechanism and chemoselectivity of the Rh-catalyzed reactions. The resulting fused azepine products are highly stable and can be further diversified.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Organic
Qiongya Li, Chunlan He, Jiahui Su, Ying Shao, Shengbiao Tang, Jiangtao Sun
Summary: We report a rhodium-catalyzed reaction that efficiently synthesizes pyridazine derivatives from N-acyl pyridazinones and diazoacetates under mild reaction conditions. This reaction likely proceeds through a carbene insertion into a C=O bond and an unprecedented 1,4-N to-O acyl rearrangement reaction.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Ruder Susanj, Vinko Nemec, Nikola Bedekovic, Dominik Cincic
Summary: In this study, the halogen bond acceptor potential of oxygen and nitrogen atoms in morpholine and piperazine fragments were investigated. Four acceptor molecules derived from acetylacetone or benzoylacetone were synthesized, and co-crystallized with 1,4-diiodotetrafluorobenzene and 1,3,5-triiodotrifluorobenzene. The results showed the formation of halogen bonds with the oxygen atom of the morpholine fragment and the nitrogen atom of the piperazine fragment. The acceptor sites of nitrogen and oxygen atoms were evaluated through calculations of molecular electrostatic potential values.
CRYSTAL GROWTH & DESIGN
(2022)
Article
Chemistry, Multidisciplinary
Constanze Keck, Jennifer Hahn, Divanshu Gupta, Holger F. Bettinger
Summary: This study reveals a highly acidic boron-nitrogen compound that can interact with silicon-containing compounds and activate their silicon bonds, providing insights into the insertion reaction mechanism.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Organic
Yongquan Ning, Qingmin Song, Paramasivam Sivaguru, Lizuo Wu, Edward A. Anderson, Xihe Bi
Summary: In this study, we reported a silver-catalyzed reaction that enables the insertion of alkynyl carbenes into beta-ketocarbonyls, providing trisubstituted allenyl ketones. This reaction represents the first example of alkynyl carbene insertion into C-C sigma bonds, resulting in products with an sp(2) carbon center. The obtained products serve as useful substrates for further transformations.
Article
Environmental Sciences
Guanyu Wang, Zihang Zhang, Dan Xu, Bo Xing, Lingjun Zhu, Shurong Wang
Summary: Pyrolysis is an important method to recover plastic monomers, fuels, and chemicals from plastic waste. However, research on the pyrolysis mechanism of plastics with C-O/C-N bonds in the backbone is still inadequate. This study comprehensively investigated the pyrolysis processes of such plastics and revealed the difficulty of breaking different backbone linkages through bond dissociation energy calculations. The results showed that PET and nylon 6 exhibited different pyrolysis behaviors, with PET decomposing primarily through the cleavage of C & alpha;-O bonds and nylon 6 degrading starting from NH2 groups at the end of the backbone.
SCIENCE OF THE TOTAL ENVIRONMENT
(2023)
Article
Chemistry, Multidisciplinary
Constanze Keck, Jennifer Hahn, Divanshu Gupta, Holger F. Bettinger
Summary: The research demonstrates that the boron-nitrogen analogue of ortho-benzyne is a reactive intermediate capable of interacting with silicon-containing single bonds and even activating and inserting into very strong Si-F bonds.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Organic
Charles E. Hendrick, Qiu Wang
JOURNAL OF ORGANIC CHEMISTRY
(2017)
Article
Chemistry, Multidisciplinary
Charles E. Hendrick, Katie J. Bitting, Seoyoung Cho, Qiu Wang
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2017)
Article
Chemistry, Multidisciplinary
Stacey L. McDonald, Charles E. Hendrick, Qiu Wang
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2014)
Article
Chemistry, Organic
Charles E. Hendrick, Qiu Wang
JOURNAL OF ORGANIC CHEMISTRY
(2015)
Article
Chemistry, Organic
Osvaldo Gutierrez, Charles E. Hendrick, Marisa C. Kozlowski
Article
Chemistry, Physical
Gang Hong, Pradip D. Nahide, Uday Kumar Neelam, Peter Amadeo, Arjun Vijeta, John M. Curto, Charles E. Hendrick, Kelsey F. VanGelder, Marisa C. Kozlowski
Article
Chemistry, Organic
Prakash Basnet, Melissa B. Sebold, Charles E. Hendrick, Marisa C. Kozlowski
Article
Chemistry, Organic
Prakash Basnet, Gang Hong, Charles E. Hendrick, Marisa C. Kozlowski
Summary: A copper-catalyzed carbochlorination reaction of alkenes with aryl malononitriles and chloride was demonstrated, yielding products that can be further converted into biologically important gamma-lactones. Mechanistic studies indicate the formation of a secondary carbon radical, which reacts with a chloride source to give the desired products. The reaction works well with both activated and unactivated alkenes, providing moderate to excellent yields.
Article
Chemistry, Medicinal
Charles E. Hendrick, Jeff R. Jorgensen, Charu Chaudhry, Iulia I. Strambeanu, Jean-Francois Brazeau, Jamie Schiffer, Zhicai Shi, Jennifer D. Venable, Scott E. Wolkenberg
Summary: A platform using a D2B approach has been developed to accelerate optimization of PROTACs through studying the linker effects. By synthesizing and characterizing a large number of linker analogs, the platform provides valuable information on the structure-activity relationships for in-cell target engagement, degradation, permeability, and cell toxicity. The platform has the potential to expand training sets for more complex prediction models.
ACS MEDICINAL CHEMISTRY LETTERS
(2022)
Article
Chemistry, Organic
Stacey L. McDonald, Charles E. Hendrick, Katie J. Bitting, Qiu Wang
