Article
Chemistry, Organic
Vladimir G. Ilkin, Valeriy O. Filimonov, Eugenia A. Seliverstova, Mikhail S. Novikov, Tetyana V. Beryozkina, Aleksey A. Gagarin, Nataliya P. Belskaya, Nibin Joy Muthipeedika, Vasiliy A. Bakulev, Wim Dehaen
Summary: In this study, a novel carbenoid-mediated approach to thioisomu'nchnones was developed, and methods to switch the reaction direction were discovered. The effect of substituents on the reaction direction was rationalized through theoretical calculations. Additionally, effective methods for the synthesis of this class of compounds were found, and some of the synthesized thioisomu'nchnones exhibited multicolor fluorescence.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Dawei Gong, Degong Kong, Yufei Li, Caiyu Gao, Lina Zhao
Summary: A nickel-catalyzed semihydrogenation of azoarenes to hydrazoarenes with NH3BH3 is developed, exhibiting good functional group tolerance and a high turnover frequency at room temperature. Control and deuterium-labeling experiments reveal that the ethanol hydroxyl and BH3 groups each donated one hydrogen, resulting in the formation of B-(OEt)(3) and H-2 as main byproducts. Density functional theory calculations suggest a ligand-to-ligand hydrogen transfer mechanism for the reaction. This study presents a novel nickel catalytic system for the semihydrogenation of azoarenes.
Article
Chemistry, Organic
John J. Monteith, Katerina Scotchburn, L. Reginald Mills, Sophie A. L. Rousseaux
Summary: A Ni-catalyzed cross-coupling reaction has been developed for the synthesis of thiocarboxylic acid derivatives using readily accessible O-alkyl xanthate esters or thiocarbonyl imidazolides and organozinc reagents. This method offers advantages such as fast reaction time, mild reaction conditions, and ease of starting material synthesis, providing a useful complementary approach for accessing a diverse range of thiocarbonyl-containing compounds compared to previously established methodologies.
Article
Chemistry, Physical
Nansalmaa Otog, Hayato Inoue, Doan Thi Thuy Trinh, Zolzaya Batgerel, Niklas Maximilian Langendorf, Ikuhide Fujisawa, Seiji Iwasa
Summary: The stereoselective synthesis of optically active cyclopropylsilanes was achieved in excellent yields and diastereo- and enantioselectivities with Ru(II)-Pheox catalysts. Among these catalysts, p-MeO-Ru(II)-Pheox was found to be the best for cyclopropanation reactions. The derivatives of cyclopropylsilanes could be transformed into beneficial building blocks for the synthesis of bioactive compounds.
Article
Chemistry, Organic
Hongyu Ding, Zhiwei Wang, Chengming Qu, Yufen Lv, Xiaohui Zhao, Wei Wei
Summary: A visible-light-mediated strategy for the synthesis of multisubstituted pyrazoles through a three-component carbene transfer reaction of alpha-diazoesters with cyclic ethers and pyrazolones is reported. This transformation can be achieved under mild and additive-free conditions, yielding a wide range of multisubstituted pyrazoles with moderate to good yields and excellent functional group compatibility. Additionally, a series of substituted 1,3-dicarbonyl derivatives can be conveniently obtained via visible-light-promoted three-component reaction of alpha-diazoesters, cyclic ethers, and 1,3-dicarbonyl compounds.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Physical
Mingjun Lv, Xiaoxun Li
Summary: This study reports a nickel-catalyzed asymmetric nitration reaction that successfully synthesized chiral oxindoles with a tertiary nitro group in good yields and high enantioselectivities. The resulting products can be used for the synthesis of chiral 3-amino oxindoles and demonstrate the synthetic potential for analogues of the antimalarial agent Cipargamin.
Article
Chemistry, Multidisciplinary
Stuart C. D. Kennington, Saul F. Teloxa, Miguel Mellado-Hidalgo, Oriol Galeote, Sabrina Puddu, Marina Bellido, Pedro Romea, Felix Urpi, Gabriel Aullon, Merce Font-Bardia
Summary: A direct and asymmetric aldol reaction of N-acyl thiazinanethiones with aromatic aldehydes catalyzed by chiral nickel(II) complexes was reported. The reaction gives high yields of O-TIPS-protected anti-aldol adducts with remarkable stereocontrol and atom economy. The removal of the achiral scaffold provides enantiomerically pure intermediates with synthetic interest for producing anti-alpha-amino-beta-hydroxy and alpha,beta-dihydroxy carboxylic derivatives, with theoretical calculations explaining the observed high stereocontrol.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Yuqi Zhu, Ting Zhou, Hong Zhang, Jieyin He, Hongguang Li, Ming Lang, Jian Wang, Shiyong Peng
Summary: This study reports a Rh(II)-catalyzed reaction method for the synthesis of α-aryl-β-aminocyclopropane carboxylic acid derivatives with stereo-isomeric centers using donor-acceptor carbenes derived from a-aryldiazoesters and vinylsulfonamides.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Multidisciplinary Sciences
Wei-Wei Yao, Ran Li, Hao Chen, Ming-Kai Chen, Yu-Xin Luan, Yi Wang, Zhi-Xiang Yu, Mengchun Ye
Summary: Allylic amines are versatile building blocks in organic synthesis and exist in bioactive compounds, but their efficient synthesis via hydroaminoalkylation of alkynes with amines has been a challenge. The authors report a late transition metal-catalyzed hydroaminoalkylation of alkynes with N-sulfonyl amines, providing a series of allylic amines in up to 94% yield.
NATURE COMMUNICATIONS
(2021)
Article
Chemistry, Organic
Jianfeng Zheng, Lin Yang, Xin Dai, Lvli Chen, Luhao Tang, Yuqiao Zhou, Wei-Dong Z. Li
Summary: Magnesium-(II)-catalyzed cascade reactions of N,N'-cyclic azomethine imines with indolyl-substituted isocyanides were conducted. The method showed high tolerance towards different functional groups and had a wide range of substrates. A series of anti-pentacyclic spiroindolines with N,N'-fused heterocycle skeletons were obtained in good yields (up to 82%) with high selectivity (8.5:1 dr) under mild conditions. Interestingly, a sequential HOAc-mediated protonation led to diastereoenriched epimerization, resulting in the formation of exclusively syn-pentacyclic spiroindolines.
Article
Chemistry, Physical
Makhosonke Ngcobo, Stephen O. Ojwach
Summary: A series of immobilized complexes were synthesized and characterized using various techniques, showing good catalytic performance in ethylene oligomerization. The type of ligand and metal atom were found to influence the catalytic performance of the complexes, and the immobilized complexes were successfully recycled for multiple uses.
MOLECULAR CATALYSIS
(2021)
Article
Chemistry, Multidisciplinary
Pallab Karjee, Manmath Mishra, Bijoy Debnath, Tharmalingam Punniyamurthy
Summary: The annulative coupling of donor-acceptor cyclopropanes with cyclic secondary amines using Ni(OTf)(2) and visible light assisted eosin Y catalysis has been reported, providing a potential synthetic tool for the construction of pyrrolotetrahydroisoquinolines.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Organic
Subhabrata Sen, Dhiraj Barman, Haya Khan, Ranajit Das, Debajit Maiti
Summary: An efficient copper-catalyzed solvent-free multi component reaction for the synthesis of pyridine derivatives, iodonium ylides, and 1,4-quinones has been developed using a room-temperature ball milling technique. This method provides a sustainable and scalable synthesis with good yields and can be used as a fluorescent chromophore-based cellular probe.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
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
Jihui Gao, Jie Ni, Rongrong Yu, Gui-Juan Cheng, Xianjie Fang
Summary: This highly regioselective nickel-based catalyst system enables the isomerization/hydrocyanation of aliphatic internal olefins, providing a variety of aliphatic nitriles with excellent regioselectivities and good yields under mild conditions. The reaction protocol, under Lewis acid-free conditions, shows broad functional group tolerance, including secondary amine and unprotected alcohol groups.