Article
Chemistry, Organic
Xin Huang, Weizhao Zhao, Yuchen Liang, Minghui Wang, Yaling Zhan, Yage Zhang, Lichun Kong, Zhi-Xiang Wang, Bo Peng
Summary: The use of difluoroenol silyl ether as a C-nucleophile in intermolecular Pummerer reaction allows for highly selective alpha-C-H difluoroalkylation of alkyl sulfoxides, including drug analogues and natural product derivatives, without the need for any additives. The success of this reaction is attributed to the electron withdrawing effect of fluorine in difluoroenol silyl ether, enabling it to distinguish different S(iv) species.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Multidisciplinary
Zhen Deng, Liu-Yan Qiu, Wenjie Pan, Baiyu Qian, Jie Chen, Hui Zhang, Qing-Yun Chen, Weiguo Cao, Xiao-Jun Tang
Summary: In this study, the classical Pummerer rearrangement efficiently produced S,O-acetal under specific conditions, and regenerated the reactive intermediate through the co-solvent, enabling the synthesis of 1-thiyl-2,2,2-trifluoroethyl arenes with excellent yields under metal-free conditions.
CHEMISTRY-AN ASIAN JOURNAL
(2022)
Article
Chemistry, Organic
Qiwen Gao, Liuting Luo, Chen Chen, Kangmei Wen, Zhibo Zhu, Xiaodong Tang
Summary: The direct utilization of amines for C-C bond formation without prefunctionalization remains a significant challenge. In this study, a base-promoted deaminative coupling of gramines with aminomalaimides under redox-neutral conditions was reported. A series of indolmethyl-substituted aminomaleimides that emitted fluorescence were synthesized in good-to-excellent yields. Biological evaluation revealed that some products exhibited antiproliferative activity against human cancer cell lines.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Takashi Mino, Yohei Fujisawa, Shizuki Yoshida, Mitsuru Hirama, Takumu Akiyama, Ryo Saito, Yasushi Yoshida, Yoshio Kasashima, Masami Sakamoto
Summary: By synthesizing cinnamoyl amide type chiral P,olefin ligand (S)-4, separable diastereomers of 4d were obtained successfully, and asymmetric allylic substitution reactions of indoles using (S,aS)-4d as a chiral ligand demonstrated high enantioselectivities (up to 98% ee).
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Organic
Takashi Mino, Kaho Takaya, Kaito Koki, Natsume Akimoto, Yasushi Yoshida, Yoshio Kasashima, Masami Sakamoto
Summary: We synthesized N-alkyl-N-cinnamoyl amide type phosphine-olefin compounds 1 and observed axial chirality in the C(aryl)-N(amide) bond of compounds 1 using HPLC analysis with a chiral stationary phase column. Enantiomeric isomers of 1 were obtained and (-)-1 was demonstrated as a chiral ligand in Pd-catalyzed asymmetric allylic substitution reactions, leading to high enantioselectivity (up to 97% ee) in the esterification process.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Organic
Guozhe Guo, Yong Yuan, Xiazhen Bao, Xuehui Cao, Tongzhi Sang, Jiayuan Wang, Congde Huo
Summary: The study presents a novel visible-light induced redox-neutral decarboxylative cross coupling reaction, which successfully synthesized a variety of symmetrical and unsymmetrical 3,3'-bisindolylmethane derivatives from indole-3-acetic acid NHPI esters and indoles. Additionally, the reaction can be easily adapted for the preparation of a wide range of diarylmethane derivatives.
Article
Chemistry, Organic
Kai Chen, Qian Liu, Jinyan Wan, Chuan Zhu, Chao Feng
Summary: A Ni-catalyzed reductive dicarbofunctionalization of α-CF3 styrenes with benzyl bromides has been achieved, which overcomes the facile β-F elimination and allows the creation of CF3-substituted all-carbon quaternary centers with pharmaceutical significance. Preliminary mechanistic studies suggest a pathway involving benzyl radical addition and subsequent nickel-mediated benzylation of the resulting α-CF3-embedded tertiary C radical.
Article
Chemistry, Organic
Takashi Mino, Toshiki Yamaoka, Kohei Watanabe, Chihiro Masuda, Shohei Kasano, Yasushi Yoshida, Ryo Takita, Yoshio Kasashima, Masami Sakamoto
Summary: P,olefin ligand/palladium catalyst systems can easily afford the corresponding 2-substituted 3-allylindole derivatives in good to excellent yields.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Subhash P. Chavan, Sanket A. Kawale, Mahesh M. Pisal, Appasaheb L. Kadam, Rajesh G. Gonnade
Summary: The diastereoselective formal synthesis of (-)-quinagolide, a D-2 receptor agonist, was achieved through three key steps, starting from L-pyroglutamic acid.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Applied
Yaoguang Sheng, Yi Gao, Bingbing Duan, Mengxia Lv, Yao Chen, Mengjie Yang, Jianmin Zhou, Guang Liang, Zengqiang Song
Summary: A versatile and efficient method for the coupling of maleimides and indoles at the C7-position has been established under Rh(III) catalysis. The protocol is compatible with various functional groups, and yields diverse 3-(indol-7-yl) maleimides and 3-(indol-7-yl)succinimides by switching reaction conditions. Deuteration studies and control experiments have been carried out to explore the mechanism of this transformation.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Multidisciplinary
Vipul V. Betkekar, Keisuke Suzuki, Ken Ohmori
Summary: The first total synthesis of parameritannin A2, a branched epicatechin tetramer, was achieved by overcoming synthetic challenges using the phloroglucinol trick. This method allowed the single-step assembly of two EC units and the successful construction of the desired structure.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Review
Chemistry, Multidisciplinary
Giovanni Centonze, Chiara Portolani, Paolo Righi, Giorgio Bencivenni
Summary: Axially chiral compounds, once viewed as merely a laboratory curiosity, have gained recognition in the past two decades for their significant role in medicinal, biological, and material chemistry. The asymmetric synthesis of atropisomers, particularly N-N atropisomers, has become a rapidly expanding field with new challenges and frontiers. This review highlights recent advances and breakthroughs in the enantioselective synthesis of N-N atropisomers, showcasing the strategies and frameworks involved.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Nicolas Zeidan, Sergiu Bicic, Robert J. Mayer, David Leboeuf, Joseph Moran
Summary: This study demonstrates that HFIP greatly expands the scope of the Bronsted acid-catalyzed hydroarylation of enamides, and acts as a slow-release reservoir for the key cationic intermediate. The reaction is fast and practical, and can prevent the oligomerization of the substrate.
Article
Chemistry, Multidisciplinary
Wei Tian, Bowen Li, Duanshuai Tian, Wenjun Tang
Summary: A palladium-catalyzed 2-alkylation of indoles with alpha-bromo esters using a P,P=O ligand has been developed. The method shows excellent regioselectivities, mild reaction conditions, and good functional group compatibility. Mechanistic studies indicate that the reaction proceeds through a radical pathway.
CHINESE CHEMICAL LETTERS
(2022)
Article
Chemistry, Organic
Liang-Hua Zou, Biao Liu, Cheng Wang, Zeyu Shao, Junqi Zhou, Andong Shao, Jian Wen
Summary: An efficient and green method for synthesizing various alkyl amines through the cleavage of vinylsulfonium salts' C(sp(3))-S bond has been developed. This reaction can be conducted under air atmosphere and shows a broad range of applicability with N-nucleophiles. Additionally, N-vinylazoles can be obtained with moderate to good yields through the reaction of vinylsulfonium salts with N-containing heterocycles in the presence of a base at room temperature.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Fuying Zhu, Yamei Lin
Summary: In this study, a low-metal iron-supported catalyst (Fe20/NC-Mg) was reported for the efficient synthesis of quinoxaline compounds, using water as a solvent and without additional bases. The synergistic effect of FeNx site and Mg (OH)2 nanorods in the catalyst played a key role in achieving high yields (82-91%) in 16 examples. The gram-level synthesis and reusability of the catalysts after four cycles demonstrated its industrial application potential.
Article
Chemistry, Organic
Mikhail Kozlov, Alexey Tyurin, Andrey Dmitrenok, Vyacheslav Rusak, Aleksander Fedorov, Igor Zavarzin, Yulia Volkova
Summary: This study presents a novel and practical synthesis method for phosphorus-substituted 1,3,4-thiadiazolines using phosphorylthioformic acid hydrazides and ketones. The protocol demonstrates operational simplicity, availability of reagents, and tolerance towards different functional groups.
Article
Chemistry, Organic
Jisna Jose, Thomas Mathew
Summary: 2-Cyclopentenone and its derivatives are highly esteemed synthetic intermediates with exceptional utility in organic synthesis. They are favored structural motifs in numerous pharmaceutical drugs and natural products, highlighting their significance. The review discusses the various methods used to synthesize cyclopentenones from 2016 to 2023.
