Article
Chemistry, Physical
Shrikant M. Khake, Ken Yamazaki, Yusuke Ano, Naoto Chatani
Summary: This study reports a branch-selective C-H alkenylation method using an iridium catalyst with alkenes, suitable for aniline derivatives containing a pyrimidine-directing group, offering a broad substrate scope and tolerating various functional groups. The origin of branch selectivity was investigated using density functional theory calculations.
Article
Chemistry, Multidisciplinary
Rikuto Tanaka, Shiho Ochiai, Asumi Sakai, Yoshinosuke Usuki, Bubwoong Kang, Tetsuro Shinada, Tetsuya Satoh
Summary: The C-H alkenylation of N-acetylcarbazoles using a cationic Cp*Rh(III) catalyst at the C1-position results in the formation of 1-alkenylcarbazoles. Further alkenylation is achieved with the use of a cationic (CpRh)-Rh-E(III) catalyst, leading to the formation of 1,8-dialkenylcarbazoles. The direct alkenylation procedure, combined with easy removal of the acetyl directing group, provides a straightforward synthetic route to 1- and/or 8-alkenyl-N-H-carbazole derivatives. One of the 1-alkenyl-N-H-carbazoles obtained in this study exhibits solvatochromism.
CHEMISTRY-AN ASIAN JOURNAL
(2023)
Article
Chemistry, Multidisciplinary
Bartlomiej Sadowski, Binbin Yuan, Zhipeng Lin, Lutz Ackermann
Summary: In this study, electrocatalytic peri C-H alkenylation of 1-naphthols was achieved using rhodium(III) catalysis under constant current electrolysis conditions. This strategy offers a wide scope, good functional group tolerance, and high site- and stereoselectivity.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Applied
Jiajie Li, Xin Xu, Zhenli Luo, Zhen Yao, Ji Yang, Xin Zhang, Lijin Xu, Peng Wang, Qian Shi
Summary: Cp*Rh(III)-catalyzed regioselective C-H annulation and alkenylation of 2-pyridones with terminal alkynes has been developed, providing efficient access to diversified compounds.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
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, 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, Multidisciplinary
Haoqiang Zhao, Zhenli Luo, Ji Yang, Bohan Li, Jiahong Han, Lijin Xu, Wenzhen Lai, Patrick J. Walsh
Summary: The first Rh-I-catalyzed, directed decarbonylative C2-H alkenylation of imidazoles with readily available alkenyl carboxylic acids is reported. The reaction provides efficient access to C2-alkenylated imidazoles that are generally inaccessible by known C-H alkenylation methods.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Applied
Ji Yang, Changjun Chen, Haoqiang Zhao, Bohan Li, Zhenni He, Lijin Xu, Qian Shi
Summary: Rh(III)-catalyzed chelation-assisted C8-selective C-H alkenylation and alkylation of 1,2,3,4-tretrahydroquinolines with styrenes and allylic alcohols have been achieved using a cationic Rh(III) catalytic system. The reaction proceeds with oxygen as the terminal oxidant and shows good substrate scope and functional group compatibility, providing the corresponding products in moderate to high yields. The choice of N-directing group is crucial for the catalysis, and the N-(2-pyrimidyl) group proves to be the optimal choice. Preliminary mechanistic studies have been conducted to gain insights into the reaction mechanism.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Physical
Seo Jin Yun, Jisu Kim, Eunsu Kang, Hoimin Jung, Hyun Tae Kim, Minkyu Kim, Jung Min Joo
Summary: The development of ligands and their roles in the catalytic cycle are crucial for achieving high efficiency and selectivity in nondirected transition-metal-catalyzed C-H functionalization. In this study, pyrazolopyridone (PzPyOH) ligands were developed for Pd-catalyzed perdeuteration and meta-selective alkenylation. The ligands facilitated C-H cleavage and enabled perdeuteration due to the incorporation of the 2-pyridone moiety, and the ligand properties allowed for selective functionalization of meta-positions in alkenylation.
Article
Chemistry, Physical
Seo Jin Yun, Jisu Kim, Eunsu Kang, Hoimin Jung, Hyun Tae Kim, Minkyu Kim, Jung Min Joo
Summary: The development of ligands and their role in catalytic cycles are essential for achieving high efficiency and selectivity in non-directed transition metal catalyzed C-H functionalization. In this study, a series of pyrazolopyridone (PzPyOH) ligands were designed for Pd-catalyzed perdeuteration and meta-selective alkenylation of arenes. The ligands incorporate a 2-pyridone moiety as an internal base, allowing for reversible C-H activation and enabling perdeuteration. The ligands also exhibit flexibility in binding to Pd, facilitating coordination with alkene coupling partners during alkenylation.
Article
Chemistry, Physical
Shrikant M. Khake, Naoto Chatani
Summary: The Rh(III)-catalyzed reaction of aniline derivatives containing a pyrimidine directing group with vinylsilanes leads to the formation of C3-substituted indoline derivatives via a highly regioselective C-H activation/alkene cyclization cascade. Mechanistic experiments suggest that C-H bond cleavage is not the rate-determining step, but rather the reaction proceeds through the formation of a six-membered rhodacycle as a key catalytic species via pyrimidine-directed electrophilic ortho-C-H rhodation.
Article
Chemistry, Organic
Jian Lin, Liuyu Hu, Chao Chen, Huijin Feng, Yang Yu, Yaxi Yang, Bing Zhou
Summary: A Rh(III)-catalyzed twofold unsymmetrical C-H alkenylation-annulation/thiolation reaction has been developed for the efficient synthesis of varied thiobenzofurans in a straightforward manner. This protocol demonstrates good functional group tolerance and broad substrate scope under mild reaction conditions.
Article
Chemistry, Applied
Ruihan Niu, Jiakai Zhao, Qi Mou, Ruyuan Zhao, Jing Zhang, Meiqi Wang, Bo Sun
Summary: An efficient and selective C-H functionalization reaction of indoles into ethynylethylene carbonates has been achieved via (CpCo)-Co-X(III) catalysis, allowing the synthesis of various vinylindoles with high yields and regioselectivity.
APPLIED ORGANOMETALLIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Manisha, Shiv Shankar Gupta, Ankit Kumar Dhiman, Upendra Sharma
Summary: An efficient Rh-catalyzed method has been developed for selective C7 halogenation of N-pyrimidyl indolines, producing corresponding halides in good to excellent yields. The strategy demonstrates broad substrate scope, excellent regioselectivity for C7 functionalization of indolines, and feasibility at gram scale level. Various control experiments were conducted to understand the reaction pathway, and the applicability of the methodology was demonstrated by synthesis of indoles and post-transformation of the C7 halogenated indolines into different valuable molecules.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Jia Yu, Si Wen, Qingyu Tian, Yanhui Chen, Guolin Cheng
Summary: In this work, a Rh(I)-catalyzed C3-alkenylation of 2,2'-bipyridine-6-carboxamide with terminal and internal alkynes was developed, providing an efficient access to a broad range of alkenylated 2,2'-bipyridine derivatives with exclusive regioselectivity and stereoselectivity. Deuterium labeling experiments indicate that an irreversible rollover C-H activation process is involved in this reaction.
SYNTHESIS-STUTTGART
(2022)
Article
Chemistry, Organic
Bo Jiao, Zhen Peng, Zhen-Hua Dai, Lei Li, He Wang, Ming-Dong Zhou
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2019)
Article
Chemistry, Organic
Chuang Liu, Yan-Jie Yang, Jun-Ying Dong, Ming-Dong Zhou, Lei Li, He Wang
JOURNAL OF ORGANIC CHEMISTRY
(2019)
Article
Nanoscience & Nanotechnology
Mingdong Zhou, Zhong Wang, Qiang Sun, Jingyun Wang, Chuanhui Zhang, Dan Chen, Xuebing Li
ACS APPLIED MATERIALS & INTERFACES
(2019)
Article
Chemistry, Organic
Ming-Dong Zhou, Zhen Peng, Lei Li, He Wang
TETRAHEDRON LETTERS
(2019)
Article
Chemistry, Organic
Hai-Wu Du, Jing Sun, Qi-Sheng Gao, Jing-Yun Wang, He Wang, Zhaoqing Xu, Ming-Dong Zhou
Article
Chemistry, Organic
Hai-Wu Du, Yang Chen, Jing Sun, Qi-Sheng Gao, He Wang, Ming-Dong Zhou
Article
Chemistry, Organic
Zhao-Hui Wang, He Wang, Hua Wang, Lei Li, Ming-Dong Zhou
Summary: This work presents a ruthenium(II)-catalyzed C-C/C-N annulation of 2-arylquinazolinones with vinylene carbonate to synthesize fused quinazolinones, showing excellent substrate tolerance and functional-group compatibility. The use of vinylene carbonate as an ethynol surrogate without external oxidants is highlighted, along with preliminary mechanistic studies and a proposed catalytic cycle.
Article
Chemistry, Organic
Lu Liu, Lei Li, Xin Wang, Ran Sun, Ming-Dong Zhou, He Wang
Summary: The synthesis of N-unprotected 2-aryl-3-cyanoindoles was achieved through Mn(III)-mediated radical cascade cyclization, using o-alkenyl aromatic isocyanides and boronic acids as substrates. The proposed mechanism involves sequential intermolecular radical addition, intramolecular cyclization, and cleavage of the C-C bond under mild reaction conditions. Mechanistic studies suggest that H2O or O-2 may provide the oxygen source for benzaldehyde elimination.
Article
Chemistry, Organic
Qi-Sheng Gao, Zhuo Niu, Yang Chen, Jing Sun, Wei-Ying Han, Jing-Yun Wang, Miao Yu, Ming-Dong Zhou
Summary: An efficient visible-light-promoted N-radical-mediated tandem radical cyclization/defluorinated alkylation of beta,gamma-unsaturated hydrazones and alpha-trifluoromethyl alkenes was described. This protocol provides a general and effective route to synthesize various dihydropyrazole-fused gem-difluoroalkenes at moderate to excellent yields under redox-neutral, metal-free, and mild conditions.
Article
Chemistry, Multidisciplinary
Fei Wang, Dan Yu, Yang Chen, Jing Sun, Jing-Yun Wang, Ming-Dong Zhou
Summary: This study reports the efficient catalytic application of a novel photosensitizer under specific conditions, with good yields and high substrate tolerance, also demonstrating its recyclability and reusability properties.
CHEMISTRY-AN ASIAN JOURNAL
(2021)
Article
Chemistry, Applied
Hua Wang, He Wang, Lei Li, Xin Wang, Ran Sun, Ming-Dong Zhou
Summary: A ruthenium(II)-catalyzed hydroamination reaction of allenoates with arylamines has been developed, providing a straightforward and efficient approach to synthesize E-allylic amines with high selectivity and atom economy.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
