Article
Chemistry, Multidisciplinary
Rong Hu, Yigao Tao, Xiaofeng Zhang, Weiping Su
Summary: In this study, a copper-catalyzed cascade reaction was reported, which produced novel γ-lactams through 1,2-aryl migration with a broad substrate scope and high yields. Mechanistically, the 1,2-aryl migration may be derived from the intramolecular amide C-N bond formation.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Kalipada Jana, Isao Mizota, Armido Studer
Summary: Formal hydroperfluoroalkylation of enones is achieved through a two-step process involving conjugate hydroboration and subsequent radical perfluoroalkylation. Both reactions proceed under very mild conditions at room temperature, making the process convenient and efficient.
Article
Multidisciplinary Sciences
Haichao Liu, Vincent Ho Man Lau, Pan Xu, Tsz Hin Chan, Zhongxing Huang
Summary: The article presents a dinuclear zinc-catalyzed desymmetric approach for the synthesis of chiral alpha-tertiary amines and tertiary alcohols. The method selectively hydrosilylates esters, enabling the synthesis of valuable structures in organic synthesis and drug discovery.
NATURE COMMUNICATIONS
(2022)
Article
Chemistry, Organic
Sixiu Liu, Jingjing Qi, Weiwei Lu, Xuan Wang, Xiaojie Lu
Summary: By utilizing a diversity-oriented synthesis strategy with alpha,beta-unsaturated carbonyl compounds, DNA-compatible transformations for various heterocyclic scaffolds have been established, paving the way for preparing DNA-encoded libraries with more extensive chemical space.
Article
Chemistry, Multidisciplinary
Yongjie Shi, Jingxin Wang, Feifan Yang, Chenhan Wang, Xumu Zhang, Pauline Chiu, Qin Yin
Summary: The efficient method described involves ruthenium-catalyzed direct asymmetric reductive amination to synthesize enantio-enriched N-unprotected alpha-amino acetals, which can be converted to various valuable molecules through convenient transformations.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Organic
Cheng Niu, Da-Ming Du
Summary: An efficient and practical organocatalytic asymmetric strategy was developed using unsaturated benzothiophenones and alpha-nitroketones catalyzed by bifunctional squaramide via Michael addition and acyl transfer steps, leading to a broad range of chiral acyloxybenzothiophene derivatives with high yields and excellent enantioselectivities. Furthermore, employing different chiral squaramide catalysts and unsaturated benzothiophenones can deliver the acyloxy unit at different positions on the benzothiophene ring.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Organic
Pedro Lopez-Mendoza, Luis D. Miranda
Summary: A simple and efficient method to obtain alpha-xanthylmethyl ketones from alpha-diazo ketones is described, using a protonation/nucleophilic substitution sequence with p-toluenesulfonic acid and potassium ethyl xanthogenate. α-Diazo ketones can be easily synthesized from ubiquitous carboxylic acids, allowing for a broad variety of xanthates to be obtained, including examples from naturally occurring substrates.
SYNTHESIS-STUTTGART
(2021)
Article
Chemistry, Organic
Zhen-Hua Wang, Tong Zhang, Qing-Fei Yan, Jian-Qiang Zhao, Yong You, Yan-Ping Zhang, Jun-Qing Yin, Wei-Cheng Yuan
Summary: In this article, various α-aryl vinylsulfonium salts were successfully transformed under mild reaction conditions, leading to the synthesis of diverse 1,2-dihydroquinoline and ring-fused tetrahydroquinoline skeletons with moderate to excellent yields. The potential application of the method was demonstrated by scale-up experiments and further derivatizations of the products. The developed protocol offers mild and transition-metal-free reaction conditions, along with easy operation.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Yan He, Qimeng Liu, Tian Gong, Yunfei Liu, Xinying Zhang, Xuesen Fan
Summary: A convenient synthesis protocol for alpha-substituted-beta-oxo azaheterocycles has been developed using oxoammonium salt-promoted cascade reaction. Nucleophiles such as acetyl or cyano group-containing active methylene compounds or morpholines were reacted with saturated cyclic amines, leading to the formation of different intermediates. The chemoselectivity of these reactions was investigated through experimental studies and DFT calculations.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Multidisciplinary
Bei Zhou, Yu-Juan He, Yun-Feng Tao, Lan-Xiang Liu, Min Hu, Zu-Hui Chang, Hong Lei, Jun Lin, Tong Lin, Guan-Ben Du
Summary: A novel electrocatalytic process was developed to prepare alpha,alpha-gem-dihalide ketones in an environmentally friendly manner. The reaction exhibited high yields of about 80% under ambient conditions without inert gas protection. The study also discovered a special dimer condensation phenomenon.
Article
Chemistry, Applied
Luxia Guo, Meng Ye, Luigi Vaccaro, Minghao Li, Yanlong Gu
Summary: A two-step protocol for the synthesis of various beta-substituted o-hydroxyphenyl ethyl ketones has been developed. The silica-supported cobalt(II) salen complex prepared using this method displayed comparable catalytic activity in synthesizing heterocycles and could be recycled multiple times without significant loss of catalytic activity.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Applied
Rikuo Hayashi, Kaori Ando, Taro Udagawa, Masahiro Sai
Summary: This study presents a method for synthesizing diverse beta-functionalized ketones from readily available 1-arylallylic alcohols in the presence of (trimethylsilyl)methylpotassium (TMSCH2K). The reaction proceeds via the formation of a highly nucleophilic dipotassio alpha,beta-dianion, which serves as a metal homoenolate equivalent and allows the one-pot synthesis of alpha,beta-difunctionalized ketones.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Organic
Chuyuan Lin, Lu Chen, Huaping Lin, Yibiao Li, Chengshuo Shen, Min Zhang
Summary: In this study, we present a new and practical approach for synthesizing aryl α,α-chlorofluoro arylketones directly in aqueous trifluoroethanol using a compatible system of selectfluor and NaCl. The method is metal-free and utilizes readily available feedstocks, demonstrating good tolerance towards functional groups. This work provides a raw material basis for the further preparation of fluorinated organic molecules.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Qiang Tang, Meng Yuan, Jiahui Duan, Keke Xu, Ruxue Li, Mengqing Xie, Shuwen Kong, Xinwei He, Yongjia Shang
Summary: A concise and efficient synthetic method for alkynyl quinolines has been established through TfOH-promoted cascade reactions, providing a variety of products with good to excellent yields. This transition-metal-free process is tolerant to halogen groups, circumventing the inherent shortcomings of existing Sonogashira coupling reactions for halogenated quinolines.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Shengneng Ying, Xingru Liu, Tao Guo, Xuan Li, Min Zhou, Xia Wang, Mengxue Zhu, Hongmei Jiang, Qing-Wen Gui
Summary: This article presents a novel and efficient method for bromination of indazoles via C-H bond cleavage to obtain site-specific 3-bromide products, which can be used as synthetic blocks in drug preparation.
Article
Chemistry, Organic
Nadezda Cankarova, Agustina La Venia, Sona Krajcovicova, Viktor Krchnak
JOURNAL OF ORGANIC CHEMISTRY
(2019)
Article
Chemistry, Applied
Jana Pospisilova, Viktor Krchnak, Eva Schutznerova
ACS COMBINATORIAL SCIENCE
(2019)
Article
Chemistry, Applied
Sergii Okorochenkov, Viktor Krchnak
ACS COMBINATORIAL SCIENCE
(2019)
Article
Biochemistry & Molecular Biology
Eva Schutznerova, Anna Krchnakova, Viktor Krchnak
Article
Chemistry, Medicinal
Rui Liu, Viktor Krchnak, Seth N. Brown, Marvin J. Miller
ACS MEDICINAL CHEMISTRY LETTERS
(2019)
Review
Chemistry, Multidisciplinary
Nadezda Cankarova, Eva Schutznerova, Viktor Krchnak
Article
Chemistry, Organic
Adam Pribylka, Viktor Krchnak, Eva Schutznerova
JOURNAL OF ORGANIC CHEMISTRY
(2020)
Article
Chemistry, Organic
Eva Schutznerov, Adam Pribylka, Noelia S. Medran, Viktor Krchnak
JOURNAL OF ORGANIC CHEMISTRY
(2020)
Review
Biochemistry & Molecular Biology
Nadezda Cankarova, Viktor Krchnak
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2020)
Article
Chemistry, Applied
Nadezda Cankarova, Ivan Nemec, Viktor Krchnak
Summary: p-TSA-mediated four-component condensation was used to synthesize diversely substituted mesoionic 1H-imidazol-3-ium-4-olates in one step. The reaction, catalyzed by p-TSA, involved the combination of an isocyanide, amine, aldehyde, and amide. The resulting mesoionic compounds, structurally related to sydnones and munchnones, are attractive intermediates and direct precursors for anionic N-heterocyclic carbenes. This one-pot synthesis offers advantages in terms of atom economy, time efficiency, and availability of starting materials.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Biochemistry & Molecular Biology
Nadezda Cankarova, Viktor Krchnak
Summary: Advanced intermediates were synthesized through Ugi four-component reactions, involving isocyanides, aldehydes, masked amino aldehyde, and carboxylic acids (including N-protected amino acids). The presence of a masked aldehyde enabled acid-mediated deprotection and subsequent cyclization. By selecting specific building blocks, diverse nitrogen-containing heterocycles, including a tricyclic framework, were obtained via regioselective cyclization of Ugi intermediates.
Article
Chemistry, Multidisciplinary
Adam Pribylka, Viktor Krchnak, Eva Schutznerova