Article
Chemistry, Organic
Huanhuan Luo, Dawei Wang, Minyan Wang, Zhuangzhi Shi
Summary: Organophosphines are important ligands widely used in organic chemistry. Although progress has been made in the construction of new phosphines through Rh- or Ru-catalyzed C-H bond functionalizations, diverse phosphines remain a challenge. The described efficient process allows for the generation of various alkenylated and 2',6'-dialkenylated biarylphosphines with high selectivity.
Article
Chemistry, Multidisciplinary
Ruijie Mi, Haohua Chen, Xukai Zhou, Nan Li, Danqing Ji, Fen Wang, Yu Lan, Xingwei Li
Summary: Axially chiral acyclic olefins were synthesized via C-H activation and olefin coupling with the assistance of a migratable directing group. Experimental results suggest different reaction pathways were utilized during the directing group migration process.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Hong-Chao Liu, Xiao-Ping Gong, Yu-Zhao Wang, Zhi-Jie Niu, Heng Yue, Xue-Yuan Liu, Yong-Min Liang
Summary: A novel Ru-catalyzed regioselective alkylarylation of vinylarenes with alkyl halides and arenes via meta-C(sp(2))-H bond functionalization has been reported. This reaction shows excellent substrate tolerance and regioselectivity, as well as redox-neutral conditions.
Article
Chemistry, Multidisciplinary
Changcheng Jing, Wenbin Mao, John F. Bower
Summary: Upon exposure to a cationic Ir(I)-complex modified with the chiral diphosphine DuanPhos, hydroalkylations of styrenes and alpha-olefins with diverse heteroaryl tert-butyl acetates occur with complete branched selectivity and very high enantioselectivity. The initial adducts undergo acid promoted decarboxylation in situ to provide alkylated heteroarenes possessing defined beta-stereocenters. The processes are postulated to proceed via a stereodefined chiral Ir-enolate, which arises upon heteroarene directed enolization of the heteroaryl acetate precursor. The method can be classified as an enantioselective decarboxylative C(sp(3))-C(sp(3)) cross-coupling.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Multidisciplinary
Takahiro Nishimura
Summary: Hydroarylation reactions using C-H activation to synthesize substituted arenes can compensate for drawbacks of classical methods like Friedel-Crafts reactions. This method involves iridium-catalyzed intermolecular and intramolecular hydroarylation reactions, including asymmetric addition reactions, depending on substrates. It utilizes a cationic iridium catalyst and various ligands to control reactivity and selectivity, along with a described H/D exchange reaction for alkenes.
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
Charline Sire, Helene Cattey, Anthonia Tsivery, Jean-Cyrille Hierso, Julien Roger
Summary: The selective C-H arylation of 1-pyrenylphosphine derivatives at the K-region using rhodium catalysis was achieved, providing isolated yields of products between 25% to 90%. Studies on intermediate species formation and reactivity supported the occurrence of a cationic rhodium catalytic process. Additionally, a large class of pyrenylphosphine ligands and their selenated derivatives were accessed, expanding the scope of functionalizable polyaromatics.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Organic
Qi-Liang Yang, Yi-Rui Luo, Rong-Yi Xu, Bei-Ning Zhang, Yan-Ni Zhang, Hai-Ming Guo
Summary: A sustainable pathway for the synthesis of tetracyclic purinium salts via ruthenium-catalyzed electro-oxidative annulation of C-6-arylpurine nucleosides with alkynes without a stoichiometric metal oxidant has been developed. The protocol exhibits high regioselectivity, broad scope, and wide functional group tolerance, allowing efficient coupling of various biologically important molecules. A novel purinoisoquinolinium-coordinated ruthenium(0) sandwich intermediate has been isolated, crystallographically characterized, and electrochemically analyzed, offering direct mechanistic insight.
Article
Chemistry, Multidisciplinary
Bingnan Du, Yuxin Ouyang, Qishu Chen, Wing-Yiu Yu
Summary: A NiH-catalyzed thioether-directed cyclometalation strategy allows for remote methylene C-H bond amidation of unactivated alkenes. This strategy shows high yields and remarkable regioselectivity in the preparation of amide products.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Organic
Sandip Kumar Gupta, Niranjan Panda
Summary: A Pd(II)-catalyzed dehydrogenative remote C4-H coupling of indoles with unfunctionalized arenes at room temperature was achieved using a weak chelating trifluoroacetyl group as a directing group. Various substituents on the arenes were compatible with the dehydrogenative cross coupling reaction.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
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
Manikantha Maraswami, Thomas Diggins, Jeffrey Goh, Raymond Tio, Wan Qing Renee Ong, Hajime Hirao, Teck-Peng Loh
Summary: This study presents a highly selective synthesis method for indene or 1-naphthol derivatives through intramolecular alkene-alkene cross-coupling, which works with different alkene pairs to give products in good to satisfactory yields. The indene products of the reaction allow further derivatization, and the reaction pathway is dependent on alkene functionalities.
Article
Chemistry, Multidisciplinary
Tomohiro Tsuda, Seung-Min Choi, Ryo Shintani
Summary: A palladium-catalyzed synthesis of new members of 5H-dibenzo-[b,f]silepins was developed, showcasing the importance and potential of developing new synthetic methods based on 1,n-metal migration processes.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Multidisciplinary
Bidhan Ghosh, Satabdi Bera, Pintu Ghosh, Rajarshi Samanta
Summary: An efficient Rh(iii)-catalyzed strategy has been developed for the synthesis of quinoline braced cyclophane macrocycles via methyl (sp(3)) C-H functionalization, which is mild, simple, regioselective, and tolerates various functional groups with different ring sizes. The method involves C8-methyl metalation, metal-carbene formation, and migratory insertion, with high dilution not necessary and nitrogen being the only byproduct. Preliminary investigation suggests that the C-H metalation step is the rate-determining step.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Organic
Rajshekhar A. Unhale, Milon M. Sadhu, Vinod K. Singh
Summary: A novel organocatalytic asymmetric formal [3 + 2] cycloaddition has been developed for the synthesis of biologically relevant chiral spiroisoindolinone-indolines with excellent yields and enantioselectivity under mild conditions.
Article
Chemistry, Applied
Hao Xiong, Xiaopeng Wu, Hepan Wang, Song Sun, Jin-Tao Yu, Jiang Cheng
ADVANCED SYNTHESIS & CATALYSIS
(2019)
Article
Chemistry, Organic
Jiangang Teng, Song Sun, Jin-Tao Yu, Jiang Cheng
JOURNAL OF ORGANIC CHEMISTRY
(2019)
Article
Chemistry, Organic
Yan Xiao, Weiming Hu, Song Sun, Jin-Tao Yu, Jiang Cheng
Article
Chemistry, Organic
Chang Wang, Peng-Cheng Qian, Fan Chen, Jiang Cheng
TETRAHEDRON LETTERS
(2020)
Article
Chemistry, Organic
Yang Li, Zhixin Wang, Shengbo Xu, Jiang Cheng
TETRAHEDRON LETTERS
(2020)
Article
Chemistry, Organic
Chen Liang, Zhibin Chen, Xinyue Hu, Shengxia Yu, Zhenlian Wang, Jiang Cheng
Summary: We developed a phosphine-catalyzed ring-opening reaction of cyclopropenones with dicarbonyl compounds as C-nucleophiles, leading to 1,3,3'-tricarbonyl compounds. This transition-metal free procedure features mild and neutral reaction conditions with good atom economy, providing an easy pathway to access 1,3,3'-tricarbonyl derivatives.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Review
Chemistry, Organic
Lu Wang, Ying Shao, Jiang Cheng
Summary: The cyanation reaction plays a key role in organic chemistry due to the wide applications of nitrile compounds. Traditionally, metal cyanides were used as cyanide sources, but recent research shows the potential of using combined cyanide sources for cyanation reactions.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Organic
Shengnan Jin, Fan Chen, Pengcheng Qian, Jiang Cheng
Summary: A new method using DTBP as a promoter allows for the difunctionalization of alpha-aryl alpha-alkynyl allylic alcohols with alkyl nitriles, resulting in alpha-alkynyl gamma-cyano functionalized ketones. This process involves C(sp(3))-H bond cleavage of alkyl nitriles and radical 3-exo-dig cyclization, with a preference for 1,2-alkynyl migration over 1,2-aryl migration.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Review
Chemistry, Organic
Chang Wang, Fan Chen, Pengcheng Qian, Jiang Cheng
Summary: The Rh-catalyzed C-H bond activation/annulation provides a new strategy for the synthesis of new frameworks, with important research significance and application prospects.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Chang Wang, Xiaodong Fan, Fan Chen, Peng-Cheng Qian, Jiang Cheng
Summary: A rhodium-catalyzed annulation of vinylene carbonate with amidines was developed in this paper, leading to 4-methylquinazolines with moderate to excellent yields. The procedure proceeded by sequential ortho-acylation and annulation, utilizing vinylene carbonate as the acetylation reagent.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Multidisciplinary
Zhixin Wang, Yang Li, Fan Chen, Peng-Cheng Qian, Jiang Cheng
Summary: A Bronsted acid-promoted intramolecular cyclization reaction was developed in the presence of TsNHNH2 to synthesize polysubstituted indenes with complexity and diversity. Unlike other reactions, a cationic cyclization pathway was involved in this method, where N-tosylhydrazone served as an electrophile and alkylation reagent.
CHEMICAL COMMUNICATIONS
(2021)
Review
Chemistry, Organic
Cong Zhou, Miao Li, Jintao Yu, Song Sun, Jiang Cheng
CHINESE JOURNAL OF ORGANIC CHEMISTRY
(2020)
Article
Chemistry, Organic
Shanshan Qiao, Peng-Cheng Qian, Fan Chen, Jiang Cheng
ORGANIC & BIOMOLECULAR CHEMISTRY
(2020)
Article
Chemistry, Multidisciplinary
Yaqun Dong, Jin-Tao Yu, Song Sun, Jiang Cheng
CHEMICAL COMMUNICATIONS
(2020)
Article
Chemistry, Organic
Yiting Li, Song Sun, Jiang Cheng, Jin-Tao Yu
ORGANIC & BIOMOLECULAR CHEMISTRY
(2020)
Article
Chemistry, Organic
Faiza Diaba, Gisela Trenchs
Summary: The first violet light-mediated synthesis of gamma- and delta-lactams from N-alkenyl trichloroacetamides is reported in this paper. The reactions are conducted in tetrahydrofuran or 2-methyltetrahydrofuran as the sole solvent without catalysts or additives, under non-anhydrous conditions in an air atmosphere where the solvent serves as the radical initiator.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Feroze Hussain, Sajjad Ahmed, Ashiq Hussain Padder, Qazi Naveed Ahmed
Summary: This study reports a novel and efficient one-pot synthesis method for mixed phosphorotrithioates, which does not require supplementary additives and shows broad applicability.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Hyunjin Oh, Ikyon Kim
Summary: A new 1,2,4-triazole-pyrrolo[1,2-a]pyrazine hybrid system, 6-acylpyrrolo[1,2-a][1,2,4]triazolo[5,1-c]pyrazine, was synthesized using a catalyst-free method. This method involved sequential exposure of pyrrole-2-carbonitrile-derived substrates to DMF-DMA and acyl hydrazide, resulting in the formation of acylated pyrazine and 1,2,4-triazole rings, enabling the installation of various substituents at specific positions on the core skeleton.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Ming Yan, Si-fan Wang, Yong-po Zhang, Jin-zhong Zhao, Zhuo Tang, Guang-xun Li
Summary: Here we developed an efficient photocatalytic approach for the convenient preparation of sulfinamides. The reaction allows for the gram-scale preparation of sulfinamides and the one-pot synthesis of various sulfonyl amides.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Farzaneh Bandehali-Naeini, Zahra Tanbakouchian, Noushin Farajinia-Lehi, Nicolas Mayer, Morteza Shiri, Martin Breugst
Summary: Two tandem catalytic systems were developed for the synthesis of novel 3,4-disubstituted maleimides using the same Ugi adducts. Different maleimide structures can be synthesized using either Pd or Cu catalysis.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Tanya Raghava, Anjan Chattopadhyay, Subhadeep Banerjee, Nivedita Sarkar
Summary: Amine substitution of two ortho fluorine atoms of tetrafluoroterephthalonitrile through SNAr chemistry is easily achievable. But further fluorine substitution is only possible under forcing conditions, yielding valuable fluorophores for bioimaging.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Review
Chemistry, Organic
Anju Chadha, Santosh Kumar Padhi, Selvaraj Stella, Sowmyalakshmi Venkataraman, Thangavelu Saravanan
Summary: Alcohol dehydrogenases are enzymes that use cofactors for oxidation or reduction reactions of alcohols or carbonyl compounds. They are utilized in green chemistry and have applications in the production of pharmaceuticals. Recombinant enzymes have solved the challenge of producing purified enzymes in large quantities. Engineered alcohol dehydrogenases have been used in asymmetric synthesis in industry. Various methods have been established for regenerating expensive cofactors to make the enzymatic process more efficient and economically viable.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)