Article
Chemistry, Organic
Yangang Wu, Wen Zhang, Shiyu Ma, Chuanjun Song, Junbiao Chang
Summary: In this study, a novel copper-catalyzed cyclization reaction was developed for the synthesis of pyrazolo-[1,5-a]-quinoline, triazolo-[1,5-a]-quinoline, and pyrrolo-[1,2-a]-quinoline derivatives. The reaction proceeds through di-tert-butyl peroxide-mediated C-(sp(3))-H activation, followed by cascade radical addition and cyclization, resulting in N-fused quinolines with high yields and broad functional group tolerance.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Zhongming Cheng, Tilong Yang, Can Li, Yunshun Deng, Fangjia Zhang, Pinhong Chen, Zhenyang Lin, Shengming Ma, Guosheng Liu
Summary: This study presents a copper-catalyzed radical relay strategy for the site-selective cyanation of sp(2) C-H bonds in allenes. The reactions show broad substrate scope and remarkable functional group compatibility under mild conditions. The site-selectivity is attributed to the unique pocket created by the Cu-bound nitrogen-centered radical and the crucial hydrogen bonding between the fluoride and the hydrogen atom. Late-stage functionalization of drug-like bioactive molecules containing an allene motif becomes feasible.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Organic
Dian Yu, Si-Yuan Peng, Han Wang, Qiu-Cui Zheng, Ya-Hui Ma, Dong-Yi Xiao, Qian-Li Li, Wen-Shu Wang, Xiao-Jie Cui, Fei-Xian Luo
Summary: In this work, a one-pot strategy was developed for the precise modification of amides derived from natural amino acids via Pd/Cu-catalyzed cascade γ-C(sp(3))-H arylation/C-N coupling. This strategy successfully synthesized valuable chiral 2-functionalized tetrahydroquinoline motifs with good chirality maintenance. It offers an alternative route for the synthesis of chiral tetrahydroquinolines with good regioselectivity and broad functional group compatibility for drug discovery. The methodology has also been demonstrated for the late-stage functionalization of natural products, drugs, and biomolecules.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Tienan Jin, Shin Suzuki, Hon Eong Ho, Hidenori Matsuyama, Masaki Kawata, Masahiro Terada
Summary: A novel Pd-catalyzed cascade reaction has been developed to construct a cyclopenta-fused acenaphtho[1,2-b]indole (ANI) scaffold, which can be used to synthesize pi-extended ANI derivatives with relatively narrow energy gaps. The potential applications of these ANI molecules as pi-segments in low-band-gap materials are implied by their increased HOMOs and lowered LUMOs.
Article
Chemistry, Organic
Hui Sun, Yi Cheng, Houyun Teng, Xiaoqi Chen, Xiaokang Niu, Hao Yang, Yu-Ming Cui, Li-Wen Xu, Lei Yang
Summary: An iridium-catalyzed, directing group-enabled site selective intra- and intermolecular silylation of indoles and pyrroles with hydrosilanes has been developed under ligand-free conditions. Fine-tuning of the removable 3-alkyl-2-pyridyl directing group was crucial for achieving high yields for C2-silylated indole and pyrrole products. Scalability and further transformations of the silylation products have also been demonstrated.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Yulei Wang, Shan Chen, Xinran Chen, Agnese Zangarelli, Lutz Ackermann
Summary: This study describes the successful catalyzed twofold remote C(sp(2))-H/C(sp(3))-H functionalizations by merging the catalyzed meta-C(sp(2))-H functionalization with aliphatic hydrogen atom transfer (HAT) process. This process is accomplished at room temperature by visible light and does not require exogenous photocatalysts.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Physical
Chao Yang, Lijun Shi, Fang Wang, Yijin Su, Ji-Bao Xia, Fuwei Li
Summary: In this study, we report a method of synthesizing chiral compounds with stereogenic bridgehead quaternary stereocenters through asymmetric catalysis of alkenylamides and alkynes. The reaction achieved high stereoselectivity and moderate-to-good yields.
Article
Chemistry, Organic
Jian Li, Hui Li, Daqing Fang, Lingjun Liu, Xu Han, Jina Sun, Chunpu Li, Yu Zhou, Deju Ye, Hong Liu
Summary: This study establishes a method for the synthesis of highly conjugated tetracyclic compounds through a Rh(III)-catalyzed reaction, characterized by high efficiency, broad substrate generality, and easy transformation.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Liexin Wu, Liping Li, Haiman Zhang, Hui Gao, Zhi Zhou, Wei Yi
Summary: A unique Rh(III)-catalyzed C-H activation/[3 + 2] annulation of N-phenoxyacetamides has been developed for the construction of dihydrobenzofurans via carbooxygenation of 1,3-dienes. This transformation features a redox-neutral process with specific chemoselectivity, good substrate/functional group compatibility, and profound synthetic potentials. Preliminary exploration for their asymmetric synthesis has been successfully demonstrated, further strengthening the practicality of this approach.
Article
Chemistry, Organic
Zhen Wang, Yi-Xin Wang, Xiao-Hui Yang
Summary: This work presents an efficient and atom-economic rhodium and thiophenol co-catalyzed hydroheteroarylation of styrenes with heteroarenes. Alkylated unprotected heteroarenes are obtained with low catalyst loading. This protocol provides a direct access to indoles bearing an all-carbon quaternary center at the C3-position.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Physical
Ruibin Wang, Sehoon Park
Summary: In this study, a one-pot, site-and stereoselective borylative reduction of quinolines was developed to obtain a series of tetrahydroquinolines with a (enantioenriched) C(sp3)-B bond in the 4-position. Mechanistic studies revealed the Rh-mediated stepwise dearomative reduction cascade. The installed C(sp3)-Bpin unit in the 4-position was transformed to various functional groups through simple organic reactions.
Article
Chemistry, Organic
Shihan Liu, Lei Zhu, Tao Zhang, Kangbao Zhong, Shi-Jun Li, Ruopeng Bai, Yu Lan
Summary: Density functional theory calculations were used to investigate the chemoselectivity of Rh-catalyzed chiral C-F cleavage and gamma-site functionalization. The results indicated that the difference in chemoselectivity in methanol and isobutyronitrile solvents can be attributed to the different controlling steps involved in beta-F elimination and allene insertion. The analysis of explicit solvent models helped explain this discrepancy.
Article
Chemistry, Organic
Yoichi Kitazawa, Takuya Kochi, Fumitoshi Kakiuchi
Summary: We present a study on the ortho-C-H alkenylation of aromatic ketones with unsymmetric internal alkynes catalyzed by an iron phosphine complex, Fe(PMe3)4. The addition of a catalytic amount of PtBu3 as an additive was shown to enhance the product yields. This alkenylation reaction displays regio- and stereoselectivity, yielding the corresponding styrene derivatives.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Yoichi Kitazawa, Takuya Kochi, Fumitoshi Kakiuchi
Summary: In this study, an ortho-C-H alkenylation of aromatic ketones with unsymmetric internal alkynes was achieved using an iron phosphine complex, Fe(PMe3)4, as the catalyst. The addition of a catalytic amount of PtBu3 improved the yield of the products. The alkenylation reaction exhibited regio- and stereoselectivity, leading to the formation of corresponding styrene derivatives.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Physical
Jian Yang, He Zhao, Zhenda Tan, Liang Cao, Huanfeng Jiang, Chenggang Ci, Pierre H. Dixneuf, Min Zhang
Summary: This study introduces a ruthenium-catalyzed method for reductive dearomatization-induced tandem functionalization, offering a general approach for constructing fused heterocycles with high functional group tolerance and broad substrate scope.
Article
Chemistry, Organic
Yan Xiao, Xiaopeng Wu, Hepan Wang, Song Sun, Jin-Tao Yu, Jiang Cheng
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)