Article
Chemistry, Multidisciplinary
Xinxin Tang, Raj K. Tak, Hidetoshi Noda, Masakatsu Shibasaki
Summary: We report the stereoselective synthesis of remotely decorated, trisubstituted beta-prolines via Rh-catalyzed C-H amination. The method works well in the presence of various functionalities, with carboxylic acids in the products serving as gateways for diverse downstream transformations.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Tao Liu, Lingli Han, Jing Zhang, Gang Lu
Summary: Density functional theory calculations were used to investigate the competing pathways of rhodacycle intermediates in Rh(III)-catalyzed annulations of 2-alkenyl phenols and 2-alkenyl anilides with alkynes. The results reveal that the multiple pathways of eight-membered rhodacycles can be subtly tuned to give specific cyclic products. The formation of different cyclic products from 2-alkenyl phenols and 2-alkenyl anilides is governed by different pathways involving the dissociation of Rh-O bond and intramolecular olefin migratory insertion, respectively.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Dibya Das, Ashis Kumar Jena, Chandan Kumar Pal, Laurens Bourda, Kristof Van Hecke
Summary: A mild, efficient, and stable copper iodide nanoparticle (CuI NP)-catalyzed method has been developed for the regioselective synthesis of 3-nitro-2-arylimidazo[1,2-a]pyridines. The method provides good to excellent yields of the desired products and the nanocatalyst showed good reusability up to three consecutive cycles. The use of molecular oxygen as an oxidant is advantageous from an economic and environmental standpoint.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Applied
Tsai-Hui Lung, Yi-Ru Chen, Chen-Ling Chang, Wey-Chyng Jeng, Pei-Shan Wu, Sandip Sambhaji Vagh, Gangababu Marri, Yi-Fang Lin, Wenwei Lin
Summary: A catalyst-controlled diversity-oriented synthesis of spirohydroquinoline-indandiones and 3-methylenehydroquinoline-indandiones was reported using ortho-sulfonamidophenyl-substituted para-quinone methides and allylidene-indandiones. Organobases such as DMAP or TMG were utilized to selectively control the reaction pathway, resulting in products with yields of 40-99% and excellent diastereoselectivities. Mechanistic studies revealed that spirohydroquinoline-indandione was the kinetic product, which underwent an unusual base-initiated 1,3-nitrogen rearrangement process to afford 3-methylenehydroquinoline-indandione in the presence of TMG.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Biochemistry & Molecular Biology
Andriani G. G. Chaidali, Ioannis N. N. Lykakis
Summary: A facile green synthetic protocol for the synthesis of several substituted N-(pyridin-2-yl)imidates was reported. The method involved the in situ formation of alpha-iminonitriles under the Lewis acid catalysis and subsequent conversion into the desired imidates using Cs2CO3 in alcoholic media. The synthetic protocol was also scalable and successfully applied for the synthesis of N-heterocycles.
Article
Chemistry, Multidisciplinary
Xiang-Ting Min, Ding-Wei Ji, Yu-Qing Guan, Shi-Yu Guo, Yan-Cheng Hu, Boshun Wan, Qing-An Chen
Summary: Transition metal catalyzed decarbonylation offers a unique synthetic strategy for new chemical bond formation. The study developed a visible light induced rhodium catalysis for decarbonylative coupling of imides with alkynes under ambient conditions, revealing the rhodium complex serves as both the catalytic center and photosensitizer. This visible light promoted catalytic decarbonylation strategy opens up new opportunities for re-evaluating old transformations with ligand dissociation as a rate-determining step.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Ze-Tian Wang, Zi-Ang Zheng, Peng-Jie Li, Chun-Ni Zhou, Shao-Jun Cai, Biao Xiao, Liang Wang
Summary: A new Rh(III)-catalyzed direct C-H alkenylation method was developed for the synthesis of terminal C2-alkenylindoles, demonstrating broad substrate scope and high functional group tolerance. The C2-alkenylated indole can be easily transformed into Carboline derivatives, important in natural products and drug molecules.
CHINESE JOURNAL OF CHEMISTRY
(2021)
Article
Chemistry, Organic
Jinhui Gu, Yongxing Zhao, Rui Li, Maozhong Miao
Summary: We describe a simple and direct rhodium(III)-catalyzed allylation-intramolecular hydroamination reaction of 5-arylsubstituted pyrazoles with allyl methyl carbonate to generate a range of 5,6-dihydropyrazolo[5,1-a] isoquinolines involving C-H bond activation and cyclization. This method exhibits good functional group compatibility and complete regioselectivity. Control experiments suggest that C-H cleavage may be the rate-determining step. (c) 2023 Elsevier Ltd. All rights reserved.
TETRAHEDRON LETTERS
(2023)
Article
Chemistry, Applied
Tobias Wagener, Marco Pierau, Arne Heusler, Frank Glorius
Summary: In this study, a one-pot protocol for the synthesis of octahydroindoles, decahydroquinolines, and octahydroindolizines through a cascade reaction is presented.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Organic
Xiaoting Gan, Fen Huang, Zhijun Ren, Bo Li, Shaojie Chen, Wenkun Luo, Jun Zhou
Summary: The synthesis of multi-substituted 1-aminoisoquinolines from aminopyridine pivalamides with alkynes by Rh(III)-catalyzed C-H activation coupling has been successfully achieved. This method is tolerant of various functional groups and provides moderate yields of highly substituted isoquinoline derivatives.
TETRAHEDRON LETTERS
(2022)
Article
Chemistry, Multidisciplinary
Yaxin Zeng, Ying Xia
Summary: The direct synthesis of gem-difluorinated carbocyclic molecules has long been a challenge in organic chemistry. Here, a Rh-catalyzed [3+2] cycloaddition reaction between gem-difluorinated cyclopropanes and internal olefins has been developed, providing an efficient method to synthesize gem-difluorinated cyclopentanes with good functional group compatibility, excellent regioselectivity, and good diastereoselectivity. The resulting products can also be further transformed into various mono-fluorinated cyclopentenes and cyclopentanes, demonstrating the potential of this reaction as a strategy for synthesizing other gem-difluorinated carbocyclic molecules.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Matthew B. B. Williams, Matthew L. L. Martin, Steffen Wiedmann, Alistair Boyer
Summary: 1,1-Dibromoalkenes can be directly used as precursors for the synthesis of 5-substituted 1,2,3-triazoles. Three different approaches, dependent on the N1 substituent, were developed to access various 1,2,3-triazole products. Treatment of 1,1-dibromoalkenes with n-butyllithium and reaction with a sulfonyl azide yielded 5-substituted 1-sulfonyl-1,2,3-triazoles. Reaction of the lithium base with zinc followed by reaction with aryl azides provided access to 1-aryl-1,2,3-triazoles. Lastly, the use of EtMgBr as base and reaction with an alkyl azide afforded 1-alkyl-1,2,3-triazoles.
SYNTHESIS-STUTTGART
(2023)
Article
Chemistry, Physical
Dan Heng, Haohua Chen, Xiaoqian He, Song Liu, Lei Zhu, Kangbao Zhong, Tao Zhang, Ruopeng Bai, Yu Lan
Summary: The dinuclear Rh(III)-Rh(III) redox catalytic cycle plays a crucial role in the remote terminal arylation of activated olefins, demonstrating greater efficiency and selectivity compared to the mononuclear rhodium catalytic cycle.
Article
Chemistry, Organic
Chen Deng, Changchang Li, Jinzhong Yao, Quanli Jin, Maozhong Miao, Hongwei Zhou
Summary: A novel rhodium-catalyzed cyclization reaction is described, allowing for the selective construction of a variety of functionalized compounds with high yields.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Daniele Ragno, Carmela De Risi, Alessandro Massi, Graziano Di Carmine, Sofia Toldo, Costanza Leonardi, Olga Bortolini
Summary: A novel NHC-promoted synthesis method for biologically active isosorbide imidates was described. The method allows the easy synthesis of different benzothiazole products by using accessible aldimines and oxidative conditions.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
