Article
Chemistry, Organic
Yi-Tan Su, Zheng-Chun Yin, Guan-Wu Wang
Summary: In this study, a palladium-catalyzed three-component alkoxyarylation reaction was conducted to synthesize a series of 1,4-(alkoxy)(aryl)[60]fullerene derivatives. Plausible reaction pathways for the formation of 1,4-(alkoxy)(aryl)[60]fullerenes were proposed. The electrochemical properties of the synthesized adducts were also investigated.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Jinliang Ma, Tong-Xin Liu, Pengling Zhang, Chuanjie Zhang, Guisheng Zhang
Summary: A new, general, and practical method for the spirocyclization of [60]fullerene has been presented through a palladium-catalyzed domino Heck/C-H activation reaction. A wide range of novel [60]fullerene-fused spirocyclic derivatives can be easily synthesized with broad substrate scope and excellent functional-group tolerance. A plausible mechanism involving an alkyl Pd(ii) species as a key intermediate has been proposed.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Multidisciplinary
Peng Shi, Yongliang Tu, Deshen Kong, Peng Wu, Ding Ma, Carsten Bolm
Summary: FeBr3-catalyzed intramolecular amidations in a ball mill lead to high yields of 3,4-dihydro-2(1H)-quinolinones. The reactions are solvent-free and easy to perform, with no need for additional ligands. Both 4-substituted aryl and beta-substituted dioxazolones provide highly selective products. Mechanistically, the formation of rearranged products is explained by an electrophilic spirocyclization followed by C-C migration.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
David Savary, Olivier Baudoin
Summary: C-H activation-based ring-forming methods are powerful for constructing complex molecular structures, especially useful for synthesizing chiral polycyclic aromatic hydrocarbons and other important organic electronic materials. A new enantioselective synthesis method using Pd-catalyzed C(sp(2))-H arylation protocol has been described, delivering diverse polycyclic compounds with high yield and good to excellent enantioselectivity, with investigation into their chiroptical properties.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Yi-Tan Su, Zheng-Chun Yin, Guan-Wu Wang
Summary: In this study, a palladium-catalyzed three-component reaction was developed for the synthesis of 1,4-aminoarylated [60]fullerene derivatives under mild conditions. Moreover, further transformations were achieved in the presence of ferric chloride.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Multidisciplinary
Matteo Corrieri, Lucia De Crescentini, Fabio Mantellini, Giacomo Mari, Stefania Santeusanio, Gianfranco Favi
Summary: A practical and environmentally friendly approach for the synthesis of pyrrolo[2,3-b]indoles has been developed using an intramolecular C-H bond amination reaction. This chemoselective transformation, which operates at 50 degrees C in water without the need for base or oxidant, relies on a Cu/Fe co-catalyst system. The easy product isolation and recyclability of the catalyst make it a promising method for the synthesis of fused N-heterocycles in pharmaceutical and medicinal chemistry.
Article
Chemistry, Multidisciplinary
Sandip B. Jadhav, Sundaram Maurya, N. Navaneetha, Rambabu Chegondi
Summary: In this study, highly diastereoselective arylative cyclization of enone-tethered cyclohexadienones via Rh(iii)-catalyzed C-H activation of N-methoxybenzamides was reported, providing access to functionalized bicyclic scaffolds with four contiguous stereocenters. The products exhibit excellent functional handles for further synthetic transformations to increase structural complexity. Mechanistic studies of arylative cyclization and a gram-scale experiment were also presented.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Organic
Muniyappa Vijaykumar, Benudhar Punji
Summary: The palladium-catalyzed chemoselective C(sp(2))-H and C(sp(3))-H acetoxylation of synthetically useful tertiary amides is reported under relatively mild reaction conditions. The reaction proceeds through the assistance of a weakly coordinated directing group and requires low catalyst loading. Diverse functionalities can be tolerated under the reaction conditions, and further functionalization to alcohols, alcohol-acids, and tertiary amines is demonstrated.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Bing Xu, Danting Ji, Lizuo Wu, Lujia Zhou, Yu Liu, Zhan-Ming Zhang, Junliang Zhang
Summary: Recent research has shown that Heck-type difunctionalization of unactivated alkenes involving C-H bond activation has emerged as a powerful strategy. However, the development of asymmetric version has been lagging behind. In this study, we demonstrate a new method for the robust Heck-type difunctionalization of a broad range of unactivated alkenes through the first palladium/Xu-Phos-catalyzed tandem Heck/remote C-H bond alkylation.
Article
Chemistry, Organic
Inaki Urruzuno, Paula Andrade-Sampedro, Arkaitz Correa
Summary: A Pd-catalyzed C(sp(2))-H acetoxylation method for Tyr-containing peptides is described, utilizing a removable 2-pyridyloxy group as a directing group. This method offers scalable and easily tunable regioselectivity for mono- and diacetoxylation reactions. Interestingly, the formation of L-DOPA peptidomimetics is hindered upon removal of the directing group.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Multidisciplinary Sciences
Shao-Long Qi, Yu-Peng Liu, Yi Li, Yu-Xin Luan, Mengchun Ye
Summary: This study investigates a novel phosphine oxide-ligated Ni-Al bimetallic catalyst, which enables the regioselective activation of β-C-H bonds in hydroarylation reactions of alkynes.
NATURE COMMUNICATIONS
(2022)
Review
Chemistry, Multidisciplinary
Asha Joshi, Zafar Iqbal, Jawahar L. Jat, Saroj R. De
Summary: In recent years, transition-metal-catalyzed chelation-controlled ortho-acylation utilizing methyl arene as the acyl partner has become a powerful technique to achieve diverse complexity, contrasting traditional cross-coupling/Friedel-Craft reactions. Diaryl ketones, as significant building blocks, are essential in pharmaceuticals, agrochemicals, natural products, and functional materials, among other useful compounds. The up-to-date developments in Pd(II)-catalyzed ortho-acylations of arenes with toluenes as acyl surrogate are studied with advantages, limitations, mechanistic pathways, and prospects.
Article
Chemistry, Organic
Yong Wang, Hui Wang, Qifan Yang, Shihua Xie, Hongjun Zhu
Summary: An efficient method for the ortho-halogenation of 2-arylquinazolines has been developed using N-halosuccinimides as halogen sources with Pd(II)-catalyzed C-H bond activation. The protocol is highly regioselective and yields up to 98% can be achieved. The mechanism of the quinazoline ortho-halogenation was investigated through comprehensive experimentation.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Bedadyuti Vedvyas Pati, Prateep Singh Sagara, Asit Ghosh, Gopal Krushna Das Adhikari, Ponneri Chandrababu Ravikumar
Summary: The study demonstrates the regioselective annulation of N-amino-7-azaindole with 1,3-diynes catalyzed by ruthenium(II). The bioactive N-amino-7-azaindole serves as a new bidentate directing group to produce a range of 3-alkynylated isoquinolones. The protocol is efficient for both aryl- and heteroaryl-substituted amides, resulting in pharmacologically useful 7-azaindole-based isoquinolones with diverse functionalities.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Youhao Wei, Zheng Wang, Kaifeng Wang, Jiang-Kai Qiu, Zhaoshan Wang, Haotian Li, Xiu Duan, Kai Guo, Xiaoguang Bao, Xinxin Wu
Summary: This study reports a copper-catalyzed allenic C(sp(2))-H cyanation with exceptional site-selectivity, addressing the challenge in synthetic chemistry of functionalizing allenic C(sp(2))-H bonds.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
