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, Physical
Samuel Hruby, Jan Ulc, Ivana Cisarova, Martin Kotora
Summary: The scope of Rh-catalyzed C-C bond cleavage/annulation of biphenylene with various aromatic nitriles was investigated. Further Rh- and Ir-catalyzed C-H bond activation/annulation sequence of the resulting 9-arylphenanthridines with alkynes led to the formation of cationic [4], [5], [6] helical quinolizinium salts. The helical arrangement of these compounds was confirmed by single-crystal X-ray analysis. Most of the prepared quinolizinium salts exhibited fluorescence emission with a maximum wavelength in the range of 525-623 nm and absolute quantum yields up to 25%.
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
Tomas J. Saiegh, Christophe Meyer, Janine Cossy
Summary: Hydroxamates derived from 3-sulfolene-3-carboxylic acid can undergo intra- and intermolecular rhodium(III)-catalyzed heteroannulations, involving C(sp(2))-H bond activation. These reactions provide a direct route to diversely substituted pyridones and pyridines fused to a sulfolene ring. The subsequent cheletropic elimination under microwave irradiation leads to the generation of pyridine ortho-quinodimethanes.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Review
Chemistry, Multidisciplinary
Takashi Koike, Munetaka Akita
Summary: The electron is unique and has the ability to participate in various systems, with novel electron injection methods revolutionizing chemical bond formation techniques in organic synthesis. In particular, visible-light organic photoredox catalysis has rapidly spread among synthetic chemists due to its sustainability and versatility.
TRENDS IN CHEMISTRY
(2021)
Article
Chemistry, Inorganic & Nuclear
Jose L. Andres, Elizabeth Suarez, Marta Martin, Eduardo Sole
Summary: This study investigates a catalyst that can transform 2-butyne into various products. Experimental and computational analyses reveal different reaction mechanisms and the crucial role of triflate in the process.
Article
Chemistry, Multidisciplinary
Yandong Wang, Jingyi Bai, Youqing Yang, Wenxuan Zhao, Yong Liang, Di Wang, Yue Zhao, Zhuangzhi Shi
Summary: A method for efficient borylation of cyclopropanes involving TM-catalysed directed C-C activation has been developed in this study, providing valuable gamma-amino boronates in a single step which are difficult to synthesize by known methods. The study also demonstrates the versatile synthetic utility of the obtained gamma-amino boronates and the preservation of chiral products. Experimental and computational mechanistic studies reveal the preferred pathway and origin of the selectivity observed.
Article
Chemistry, Applied
Yuna Nishiguchi, Katsuhiko Moriyama
Summary: A new synthetic method was developed with the use of aniline-type hypervalent iodine(III) for direct cyclizations, resulting in high yields of the corresponding products.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Review
Chemistry, Applied
Xiaofan Cui, Remi Chauvin, Chao Pi, Yangjie Wu, Xiuling Cui
Summary: This review presents recent progress in the use of vinylene carbonate as a reactant in transition metal-catalyzed C-H bond activation/cyclization reactions. By analyzing and comparing different reaction models, it highlights the advantages of using vinylene carbonate as a surrogate for ethynol and other reactants, and discusses related mechanisms and synthetic applications.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Review
Chemistry, Organic
Nitin Tandon, Rekha Thakur, Runjhun Tandon, Iqubal Singh, Kamaldeep Paul, Aeyaz Ahmad Bhat
Summary: Replacement of traditionally unreactive C-H bond with C-C or C-X has become a widely accepted method for synthesizing complex organic molecules, which can serve as important intermediates for biologically active compounds. However, selective functionalization of the C-H bond remains a challenge for synthetic organic chemists. This review summarizes various synthetic strategies, including the use of metal catalysts, to achieve C-H bond functionalization and the development of targeted complex molecules with medicinal properties.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Takanobu Saito, Joaquim Caner, Naoyuki Toriumi, Nobuharu Iwasawa
Summary: A novel method for the meta-selective C-H carboxylation of 1,1-diarylethylene derivatives using a rhodium catalyst and a stoichiometric reductant has been achieved. The introduction of a carboxyl group to the aryl ring at the meta-position was enabled with high selectivity. Both experimental and computational mechanistic studies indicate that a specific rhodium migration process plays a key role in this unusual aryl-to-aryl 1,2-rhodium shift.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Applied
Hisanori Nambu, Ryoya Amano, Takafumi Tamura, Takayuki Yakura
Summary: This study describes the dirhodium(II)-catalyzed intramolecular insertion of aryldiazoacetates into unactivated primary C-H bonds. The reaction shows high selectivity and provides a direct route to 2-unsubstituted indane-1-carboxylates and specific isomers with ortho-substituted groups. Furthermore, a chemoselective C-H insertion reaction of aryldiazoacetate with a 1-oxyethyl substituent is achieved using a specific protecting group.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Review
Chemistry, Applied
Ahmad Saifuddin Mohamad Arshad, Mohd Nizam Mordi
Summary: Carbolines are a prominent class of tricyclic alkaloids found in natural products, and there are four different regioisomers known. Synthetic methods have been established for the construction of carboline frameworks, both requiring customized approaches for each regioisomer and unified approaches capable of generating multiple regioisomers. This review summarizes the construction of isomeric carbolines based on unified synthetic approaches.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Organic
Youliang Zou, Binfeng Zhang, Li Wang, Hua Zhang
Summary: A benzoic acid-promoted C2-H borylation of indoles with pinacolborane is developed, providing a prompt route toward the synthesis of diverse C2-functionalized indoles. Preliminary mechanistic studies suggest that BH3-related borane species formed via the decomposition of pinacolborane may be the probable catalyst.
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)
