Article
Chemistry, Organic
Shangyuan Wang, Jiangjie Zhang, Jian-Shu Wang, Jun Ying, Xiao-Feng Wu
Summary: A palladium-catalyzed cascade radical cyclization and carbonylation reaction of 1,7-enynes with perfluoroalkyl iodides and alcohols has been developed. The use of benzene-1,3,5-triyl triformate (TFBen) as the CO source enables the construction of 3,4-dihydroquinolin-2(1H)-one skeletons with the incorporation of both perfluoroalkyl and carbonyl units. This method provides a facile and efficient approach for the synthesis of various 3,4-dihydroquinolin-2(1H)-one derivatives with moderate to high yields and excellent E/Z selectivity.
Article
Chemistry, Multidisciplinary
Yang Gao, Haixia Li, Simin Yang, Yanping Huo, Qian Chen, Xianwei Li, Zhe Wang, Xiao-Qiang Hu
Summary: In this study, a novel copper-catalyzed reaction was developed for the synthesis of highly reactive ynamine compounds from terminal alkynes. These compounds were utilized for the modular synthesis of diverse quinoline derivatives. The method also allowed for the synthesis of quinoline-fused heterocycles and the modification of complex molecules, demonstrating its practicality and versatility.
SCIENCE CHINA-CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Suchen Zou, Zeyu Zhao, Hanmin Huang
Summary: In this study, a novel and efficient palladium-catalyzed reaction was developed for the regioselective and stereodivergent ring-closing of aminoenynes with aldehydes and boronic acids or hydrosilane. The reaction allows for the synthesis of a series of exocyclic 1,3-dienes bearing saturated N-heterocycles of 5- to 8-membered rings. It utilizes a simple Pd-catalyst and works under mild reaction conditions with a broad range of substrates. The resulting products serve as useful intermediates for chemical synthesis due to the versatility of the conjugated diene. Preliminary mechanistic details of the reaction are also uncovered.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Yanfeng Ma, Chunlan Zhou, Fuhong Xiao, Guojiang Mao, Guo-Jun Deng
Summary: A metal-free method for synthesizing 2-substituted quinolines and benzo[f]quinolines from aromatic amines, aldehydes, and tertiary amines has been developed. Cheap and readily available tertiary amines were used as the vinyl source, and a new pyridine ring was selectively formed through [4 + 2] condensation promoted by ammonium salt under neutral conditions and an oxygen atmosphere. This strategy offers a new route for preparing various quinoline derivatives with different substituents, allowing for further modifications.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Wei Hu, Chao Pi, Di Hu, Xiliang Han, Yangjie Wu, Xiuling Cui
Summary: A rhodium-catalyzed cyclization of azobenzenes and vinylene carbonate has been developed to construct indazolo[2,3-a]quinolines. This method offers high yields and broad functional group tolerance, forming three C-C bonds and one C-N bond in one pot. Additionally, the resulting products exhibit favorable fluorescence properties.
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
Shi-Yin Tian, Jing-Jing Ai, Jia-Hui Han, Weidong Rao, Shu-Su Shen, Daopeng Sheng, Shun-Yi Wang
Summary: A photocatalytic synthesis method was developed to simultaneously construct two C-S/Se bonds and one C-C bond without the use of transition metals or other additives, using diphenyl disulfide or diphenyl diselenide as sulfur or selenium sources.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Zi-Qi Zhang, Yi-Hao Xu, Jing-Cheng Dai, Yan Li, Jie Sheng, Xi-Sheng Wang
Summary: A facile and efficient approach for the synthesis of CF3-containing dioxodibenzothiazepines has been developed via copper-catalyzed trifluoromethylation/cyclization of alkynes utilizing a radical relay strategy. This method demonstrates low catalyst loading, high regiocontrol, and broad scope under mild conditions, proving its versatility and potential for further derivatization.
Article
Chemistry, Organic
Sukanya De, Chinmay Chowdhury
Summary: A simple and efficient method for the synthesis of 4-(2,2-diarylvinyl)-quinolines and 4-(2,2-diarylvinyl)-2H-chromenes has been developed using Fe-(III)-catalyzed intramolecular annulations of homopropargyl substrates. The high yields (up to 98%) achieved with simple substrates, an environmentally benign low-cost catalyst, and less hazardous reaction conditions make this methodology inherently attractive.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Shivam A. A. Meena, Poonam Sharma, Akhilesh K. K. Verma
Summary: A transition-metal-free one-pot synthesis of di-functionalized succinimides has been developed, which involves a radical cascade seleno/thiosulfonation of aza-1,6-enynes in an atom economical manner. This method allows the synthesis of highly decorated succinimides with excellent stereoselectivity under mild reaction conditions. The proposed radical pathway is well supported by control experiments. The reaction demonstrates advantageous features including operational simplicity, atom economy, and broad substrate scope.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Organic
Jiaao Ge, Hongli Wu, Deping Kong, Genping Huang
Summary: Density functional theory calculations were used to investigate the cobalt-catalyzed intermolecular hydroacylation/cyclization of 1,6-enynes with aldehydes. The study showed that the initial oxidative cyclization is the rate-determining step of the overall reaction, and the enantioselectivity is mainly caused by steric repulsion between the aldehyde moiety and the aryl substituent of the 1,6-enyne.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Xiaochen Chi, Tong Xia, Yi Yang, Tong Cao, Daopeng Zhang, Hui Liu
Summary: In this study, a novel diastereoselective synthesis strategy was reported to construct the octahydro-1H-cyclopenta[c]pyridine skeleton from (Z)-1-iodo-1,6-diene and alkyne via Pd/Au-relay catalyzed sequential intramolecular Heck-type cyclization, Sonogashira coupling, and 1,5-enyne cyclization. The strategy exhibited excellent diastereoselectivity and synthetic efficiency, and is expected to play an important role in natural product synthesis and drug development.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Zhi Zhang, Jing-Tong Deng, Jia-Yi Feng, Jin-Yan Liang, Xue-Tao Xu, Jin-Bao Peng
Summary: A palladium-catalyzed annulation of o-iodo-anilines with propargyl alcohols for the synthesis of substituted quinolines has been developed. The reaction shows tolerance towards diverse functional groups under mild conditions, providing a direct access to 2,4-disubstituted quinolines from easily available starting materials. A broad range of 2,4-disubstituted quinolines were efficiently synthesized in good to excellent yields.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Quentin Dherbassy, Srimanta Manna, Chunling Shi, Watcharapon Prasitwatcharakorn, Giacomo E. M. Crisenza, Gregory J. P. Perry, David J. Procter
Summary: In this study, an enantioselective copper-catalyzed borylative cyclization was reported for the assembly of privileged pyrroloquinazolinone motifs. The reaction demonstrated high enantio- and diastereocontrol, yielding products with quaternary stereocenters. The utility of the products was further demonstrated through additional manipulations.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Hui Chen, Yunyun Yan, Niuniu Zhang, Zuyu Mo, Yanli Xu, Yanyan Chen
Summary: A visible-light-induced cascade reaction of 2-vinyloxy arylalkynes with thiosulfonates was developed, yielding unexpected thio-substituted dibenzofuran derivatives in moderate yields. Mechanistic studies revealed the key intermediate in this reaction and the role of the additive disulfide in the aromatization process, presenting a new reaction mode for the construction of polycyclic oxygen heterocycles.
