Article
Chemistry, Multidisciplinary
Ruizhi Lai, Shuran Xu, Qingyao Zhang, Hui Zhou, Cankun Luo, Yuerong Wang, Li Hai, Yong Wu
Summary: A method for the synthesis of benzothiadiazine-1,1-dioxide and spiro benzothiadiazine derivatives through transition metal-catalyzed C-H activation/annulation was reported. The reaction substrates used were 3-phenyl-2H-benzothiadiazine-1,1-dioxide, and the coupling reagents used were vinylene carbonate and 4-diazopyrazolone. This strategy provides a straightforward and highly efficient approach to complex N-heterocycles.
CHINESE JOURNAL OF CHEMISTRY
(2023)
Article
Chemistry, Organic
Yan Long, Yun Wang, Yue-You Chen, Wen-Yong Han, Nan-Wei Wan, Wei-Cheng Yuan, Yong-Zheng Chen, Bao-Dong Cui
Summary: This article describes an inexpensive copper-catalyzed sequential reaction process for synthesizing structurally diverse spiro-dihydropmolo[1,2-a]quinoxaline derivatives. The significance of this method is highlighted by its ability to convert synthetic compounds into potentially bioactive molecules.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Andres Arribas, Martin Calvelo, David F. Fernandez, Catarina A. B. Rodrigues, Jose L. Mascarenas, Fernando Lopez
Summary: The study presents a versatile and highly enantioselective intramolecular hydrocarbonation reaction for the synthesis of heteropolycyclic systems with chiral quaternary carbon stereocenters. The method relies on an iridium-(I)/bisphosphine chiral catalyst, yielding fused indole and pyrrole products with high enantiomeric excesses. DFT computational studies provided a detailed mechanistic profile and identified weak non-covalent interactions as key factors controlling the enantioselectivity.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Physical
Raju S. Thombal, Peter Yuosef M. Rubio, Daesung Lee, Debabrata Maiti, Yong Rok Lee
Summary: Metal catalyzed cascade C-H activation/annulation is a highly promising approach for the construction of aromatic and heteroaromatic compounds. Pd-complexes play a crucial role in this method, enabling high catalytic efficiency through the activation of molecules bearing a directing group.
Article
Chemistry, Applied
Manqing Wang, Qianting Zhou, Xinying Zhang, Xuesen Fan
Summary: A condition-controlled divergent synthesis of imidazoindolone spiro-isoquinolinones (IISIQs) was presented, which involved the cascade reactions of N-alkoxycarboxamide indoles with diazo homophthalimides. Under different conditions, two different types of IISIQ compounds, IISIQ-OR and IISIQ-H, were formed. This method provides a versatile approach for the synthesis of diverse spiroheterocyclic scaffolds.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Organic
Shenghai Guo, Ziyi Zhang, Zhaotong Wei, Yuanqing Zhu, Xuesen Fan
Summary: An efficient strategy for the preparation of spirocyclic indole-N-oxide compounds through a Rh(III)-catalyzed [4 + 1] spiroannulation reaction of N-aryl nitrones with 2-diazo-1,3-indandiones as C1 synthons under extremely mild conditions is presented. From this reaction, 40 spirocyclic indole-N-oxides were easily obtained in up to 98% yield. In addition, the title compounds could be successfully used for the construction of structurally intriguing maleimide-containing fused polycyclic scaffolds via a diastereoselective 1,3-dipolar cycloaddition reaction with maleimides.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Review
Chemistry, Multidisciplinary
Neha Jha, Nandkishor Prakash Khot, Manmohan Kapur
Summary: The past decade has seen significant advancements in transition-metal-catalyzed C-H bond activation and carbene migratory insertion reactions, facilitating the construction of diverse arene/heteroarene scaffolds. Various transition-metal catalysts are utilized for easy access to substituted heterocycles, with key mechanistic pathways involving C-H activation, diazo insertion, and subsequent coupling reactions.
Article
Chemistry, Applied
Min Liu, Kelu Yan, Jiangwei Wen, Xue Li, Xiaoyu Wang, Fengjie Lu, Xiu Wang, Hua Wang
Summary: The rhodium(III)-catalyzed C-H/diazo coupling and tandem annulation of 3-oxopent-4-enenitriles have been proposed for the synthesis of polysubstituted phenols, yielding most products in good yields. Preliminary mechanistic studies and derivatization reactions of phenol products were also conducted, offering an alternative approach for synthesizing a variety of useful phenols.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Applied
Kenji Matsumoto, Rina Nakano, Ken-ichi Yamada, Tsukasa Hirokane, Masahiro Yoshida
Summary: This study reports an efficient platform for the one-step construction of nitrogen-containing polycyclic frameworks using a heterogeneous platinum-catalyzed oxidative alpha,beta-C(sp(3))-H dual functionalization of saturated cyclic amines. By conducting a tandem oxidative dehydrogenation/hetero Diels-Alder reaction under mild aerobic conditions, tetracyclic octahydro-dipyrroloquinoline frameworks were synthesized in good yields. The reaction was successfully applied to the one-step synthesis of natural products incargranine B aglycone and seneciobipyrrolidine. This study provides an efficient and rapid approach to nitrogen-containing fused tetracyclic compounds in a highly atom-economical manner.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Multidisciplinary
Kristine Klimovica, Julius X. Heidlas, Irvin Romero, Thanh V. Le, Olafs Daugulis
Summary: This article reports sandwich diimine-copper(I) catalysts for C(sp(3))-H bond functionalization, demonstrating rare examples of base-metal catalyzed, intermolecular C(sp(3))-H functionalizations using unactivated diazo compounds. The electrophilicity and unique steric environment of the sandwich-copper catalysts are likely reasons for their catalytic efficiency.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Applied
Yasuaki Fukazawa, Vladimir Yu. Vaganov, Julia V. Burykina, Artem N. Fakhrutdinov, Ruslan I. Safiullin, Felix Plasser, Aleksandr E. Rubtsov, Valentine P. Ananikov, Andrei V. Malkov
Summary: The mechanism of metal-catalyzed asymmetric alkylation of indoles remains uncertain. In this study, the authors investigate the mechanism from both molecular and nano-level perspectives, revealing the role of water and catalyst precursor on reaction selectivity and performance.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Multidisciplinary
Kai Wu, Xuyang Zhang, Liang-Liang Wu, Jie-Sheng Huang, Chi-Ming Che
Summary: In this study, we reported a modular approach to the synthesis of trifluoromethyl-bearing 5-membered rings through direct rhodium-catalyzed carbene insertion into C(sp(3))-H bonds. The reaction showed good control over site- and stereochemistry, and was applicable for the synthesis of chiral CF3 analogues. Stoichiometric reactions of ruthenium carbene complexes provided evidence for the involvement of metal carbene species in the catalytic cycle. DFT calculations explained the origin of selectivity in the benzylic C-H insertion reactions.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Review
Chemistry, Multidisciplinary
Sandeep Kumar, Akshay Kumar, Dharminder Sharma, Pralay Das
Summary: Directing groups are widely used for transition metal-catalyzed direct C-H bond functionalization, with recent advancements in utilizing free amine, hydroxyl and sulfhydryl as directing groups for the synthesis of heterocycles.
Article
Chemistry, Organic
Qinghe Gao, Zhenhua Sun, Qinfei Xia, Ruonan Li, Wenlong Wang, Siwei Ma, Yixin Chai, Manman Wu, Wei Hu, Peter Abranyi-Balogh, Gyorgy M. Keseru, Xinya Han
Summary: A new general synthesis method has been developed to prepare pharmaceutically important azolo[1,5-a]pyrimidines starting from commonly available 3(5)-aminoazoles, aldehydes, and triethylamine. This direct and practical strategy allows the construction of a variety of compounds, including pyrazolo[1,5-a]pyrimidines and [1,2,4]triazolo[1,5-a]pyrimidines, with the capability to synthesize zaleplon, a clinically used drug.
Article
Chemistry, Organic
Narasingan Aravindan, Masilamani Jeganmohan
Summary: An efficient synthesis of benzo-[c]-phenanthridine alkaloids via a synergistic combination of C-C bond formation and a cycloaromatization reaction is described. Aryl nitrones react with 7-azabenzonorbornadienes in the presence of a Rh-(III) catalyst, providing pharmaceutically useful benzo-[c]-phenanthridine derivatives in good to moderate yields. Using this methodology, highly useful alkaloids such as norfagaronine, norchelerythrine, decarine, norsanguinarine, and nornitidine were prepared in a single step.
