Article
Chemistry, Physical
Xavier Abel-Snape, Gina Wycich, Mark Lautens
Summary: A palladium-catalyzed three-component domino reaction for accessing indene derivatives is described. The reaction involves the sequential formation of three bonds, with the first two resulting from inter- and intramolecular carbopalladation, and the final bond arising from an attack by a terminating nucleophilic reagent. The starting tether on the iodoarene can be modified to yield either indenes or benzofulvenes. Additionally, the use of an oxabicycle as an acetylene surrogate is demonstrated, and the enantioselective synthesis of indenes is preliminarily explored.
Article
Chemistry, Organic
Yu Sun, Jiayu Pan, Xiuqi Wang, Xiaoli Bu, Mengtao Ma, Fei Xue
Summary: A rhodium-catalyzed tandem arylation/cyclization reaction of 3-(ortho-boronated aryl) conjugated enones with unactivated alkynes is described. The use of a rhodium(I)/chiral-diene complex as the catalyst afforded various 2,3-disubstituted indene compounds with high yields, excellent regioselectivities, and enantioselectivities. This approach is attractive as it utilizes simple starting materials such as diarylalkynes, dialkylalkynes, and alkyl(aryl)alkynes.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Guangwu Sun, Herui Liu, Xiu Wang, Wenbo Zhang, Wenjun Miao, Qinyu Luo, Bing Gao, Jinbo Hu
Summary: In this manuscript, a novel palladium-catalyzed coupling reaction between gem-difluoroalkenes and aryl boronic acids is reported, which yields bioactive indane-type ketones with an all-carbon alpha-quaternary center. The mechanism involves a water-induced defluorination and cross-coupling cascade pathway, supported by characterization and stoichiometric reactions of the key intermediates RCF2PdII. The use of vinyl difluoromethylene motif as an in situ carbonyl precursor is unprecedented in transition-metal-catalyzed coupling reactions, and it is expected to spark broad interest in ketone synthesis, fluoroalkene functionalization, and design of new synthetic protocols based on the unique reactivity of difluoroalkyl palladium(II) species.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Dong Wei, Han-Yu Lu, Han-Zhe Miao, Chen-Guo Feng, Guo-Qiang Lin, Yingbin Liu
Summary: An efficient and environmentally friendly method for preparing substituted indene derivatives using water as the sole solvent has been developed. This reaction can be conducted under air, tolerates a wide range of functional groups, and can be easily scaled up. Bioactive natural products like indriline can be synthesized using this protocol. Preliminary results show the possibility of achieving enantioselectivity.
Article
Chemistry, Organic
Qian-Qian Ma, Cheng-Jing Li, Wei-Wei Liao
Summary: An efficient method for constructing alpha-amino cyclopentanones with consecutive quaternary and ternary carbon centers is described using an alpha-iminol rearrangement and Pd-catalyzed addition reaction. The method offers high yields, excellent selectivity, and can be used to prepare high-value added compounds.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Tao Zhang, Cheng Zhang, Xiunan Lu, Chengxing Peng, Yawei Zhang, Xiong Zhu, Guofu Zhong, Jian Zhang
Summary: A ruthenium-catalyzed C-H alkylation/cyclization sequence has been developed for the synthesis of silyl indenes with atom and step-economy. This reaction is triggered by acyl silane-directed C-H activation and controlled by an aldehyde for following enol cyclization/condensation. The protocol exhibits broad tolerance for substitution patterns, and the synthetic elaboration of silyl indenes provides access to a diverse range of interesting indene and indanone derivatives.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Yang Yuan, Fu-Peng Wu, Anke Spannenberg, Xiao-Feng Wu
Summary: An efficient strategy for synthesizing beta-geminal-diboryl ketones through a Cu/Pd-catalyzed borocarbonylative trifunctionalization of readily available alkynes and allenes has been reported. This method shows broad functional group tolerance and has the potential to advance the field of organic synthesis. Mechanistic studies suggest that the reaction proceeds through a borocarbonylation/hydroboration cascade of both alkynes and allenes.
SCIENCE CHINA-CHEMISTRY
(2021)
Article
Chemistry, Applied
Jiaqing Xu, Wangyu Shi, Min Liu, Jianning Liao, Wei Wang, Yongjun Wu, Hongchao Guo
Summary: A palladium-catalyzed [4+2] cycloaddition reaction has been developed for the efficient synthesis of tetrahydropyran derivatives with good selectivity.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Organic
Yetong Zhang, Lepeng Chen, Yinlin Shao, Fangjun Zhang, Zhongyan Chen, Ningning Lv, Jiuxi Chen, Renhao Li
Summary: The study presents a three-component tandem reaction allowing the synthesis of polysubstitution quinolines using 2-aminobenzonitriles, arylboronic acids, and ketones. This method is practical, efficient, and delivers functional quinolines with moderate to good yields and high functional group tolerance. Additionally, a new method for introducing halogen substituents into the target products has been developed, showing potential for further synthetic elaborations.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Organic
Shao-Yu Zou, Fang Yang, Xin Zhao, Xin-Ge Ren, Zi-Sheng Chen, Kegong Ji
Summary: A ligand-enabled Cu(II)-catalyzed approach was developed for highly selective synthesis of 2E-alkenylfurans 2 from ynenones under an air atmosphere. The amide group on the designed 1,10-phenanthroline framework played a key role in promoting the internal 1,2-migration and stabilizing the carbocation. The Cu(II) catalyst, with the bifunctional ligand L1, exhibited high efficiency in catalyzing ynenones to 2E-alkenylfurans 2 at room temperature in excellent yields under air atmosphere.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Physical
Xing Ge, Xiuyu Fang, Ren-Guan Miao, Xinxin Qi, Xiao-Feng Wu
Summary: A general and efficient protocol has been developed for the synthesis of acetamide-functionalized benzofurans using a palladium-catalyzed intramolecular cyclization and reductive aminocarbonylation reaction. The reaction proceeds in a single step, resulting in structure-defined benzofurans with acetamides as attractive functional groups. Various acetamide-functionalized benzofurans were obtained with moderate to good yields and good functional group compatibility using Mo(CO)6 as both CO source and reductant.
JOURNAL OF CATALYSIS
(2023)
Article
Chemistry, Applied
Haeun Park, Sunwoo Lee
Summary: The Friedel-Crafts acylation reaction was conducted between activated amides and arenes using [Pd(cinnamyl)Cl](2) and Cu(OTf)(2) as catalysts. A variety of N-phenyl-N-tosylbenzamides with substituted phenyl rings underwent reactions with different arenes, including mesitylene, toluene, anisole, 4-tert-butylbenzene, o-xylene, m-xylene, and p-xylene, resulting in the corresponding diaryl ketones with yields ranging from 49% to 89%.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Organic
Wei-Xiang Zheng, Jing Zhong, Yi-Ting Yang, Meluze Luobu, Yan Zhang, Yuan-Hua Wang, Qi-Wei Wang
Summary: Carboxylic acids are commonly used stable reagents in organic synthesis, but their direct use as substrates in the Suzuki-Miyaura coupling reaction is rarely reported. This study presents an efficient coupling reaction between carboxylic acids and arylboronic acids, yielding the corresponding aryl ketones.
SYNTHESIS-STUTTGART
(2022)
Article
Chemistry, Organic
Min Zeng, Fuli Huang, Minghui Zhu, Jichao Ding, Tong Qin, Maoting Xu, Wanqing Liu, Jun Lu, Jicheng Wu, Xurong Qin, Qiao Ren
Summary: Despite the availability of chemical feedstocks, developing useful cross-coupling reactions with methyl esters as acyl electrophiles is still challenging due to their chemical inertness. We present a simple nickel-catalyzed intramolecular alkene hydroacylation method for the efficient synthesis of various medicinally active indanone and indazolone derivatives. This approach offers good functional group tolerance, easy post-synthetic modifications, total synthesis, and fluorescent probe synthesis. Preliminary in vitro antioxidant evaluation reveals promising free radical scavenging activities of 2-(4-dimethylaminophenyl)-1-indanone and 2-aryl-3-indazolone derivatives.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Xiao-Jiao Feng, Jian-Guo Fu, Qian Zhao, Yu-Han Lu, Shu-Sheng Zhang, Chen-Guo Feng
Summary: Palladium-catalyzed cross-coupling of ortho-alkenyl bromobenzenes and a-aryl-a-diazoesters was achieved, resulting in moderate to excellent yields and a wide substrate scope. This provides a straightforward approach for synthesizing 1,1-disubstituted indenes. The reaction likely proceeds through a tandem alkenyl C-H activation/carbene insertion sequence, with a C,C-pallada(II)cycle as the key intermediate.
SYNTHESIS-STUTTGART
(2023)
Article
Chemistry, Multidisciplinary
Hang Gong, Huiying Zeng, Feng Zhou, Chao-Jun Li
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2015)
Article
Chemistry, Organic
Simon A. Girard, Huawen Huang, Feng Zhou, Guo-Jun Deng, Chao-Jun Li
ORGANIC CHEMISTRY FRONTIERS
(2015)
Article
Chemistry, Organic
Feng Zhou, Xiaoyun Hu, Wanying Zhang, Chao-Jun Li
JOURNAL OF ORGANIC CHEMISTRY
(2018)
Article
Chemistry, Multidisciplinary
Zhenhua Jia, Feng Zhou, Mingxin Liu, Xingshu Li, Albert S. C. Chan, Chao-Jun Li
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2013)
Article
Chemistry, Multidisciplinary
Feng Zhou, Marc-Oliver Simon, Chao-Jun Li
CHEMISTRY-A EUROPEAN JOURNAL
(2013)
Article
Chemistry, Multidisciplinary
Ping Wang, Honghua Rao, Feng Zhou, Ruimao Hua, Chao-Jun Li
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2012)
Article
Chemistry, Organic
Feng Zhou, Miao Yang, Xiyan Lu
Article
Chemistry, Organic
Simon A. Girard, Xiong Hu, Thomas Knauber, Feng Zhou, Marc-Olivier Simon, Guo-Jun Deng, Chao-Jun Li
Article
Chemistry, Organic
Feng Zhou, Xiuling Han, Xiyan Lu
TETRAHEDRON LETTERS
(2011)
Article
Multidisciplinary Sciences
Feng Zhou, Chao-Jun Li
NATURE COMMUNICATIONS
(2014)
Review
Chemistry, Multidisciplinary
Alejandra Dominguez-Huerta, Xi-Jie Dai, Feng Zhou, Pierre Querard, Zihang Qiu, Sosthene Ung, Wenbo Liu, Jianbin Li, Chao-Jun Li
CANADIAN JOURNAL OF CHEMISTRY
(2019)
Article
Chemistry, Multidisciplinary
Feng Zhou, Zoe Hearne, Chao-Jun Li
CURRENT OPINION IN GREEN AND SUSTAINABLE CHEMISTRY
(2019)
Article
Chemistry, Multidisciplinary
Feng Zhou, Chao-Jun Li
Article
Chemistry, Organic
Feng Zhou, Xiaoyun Hu, Wanying Zhang, Chao-Jun Li
ORGANIC CHEMISTRY FRONTIERS
(2018)