Article
Chemistry, Organic
Wei Dong, Zhuo-Yue Fang, Tong-Yang Cao, Jie-Hui Cao, Zi-Qiang Zhao, Linlin Zhang, Wei Li, Lin Qi, Li-Jing Wang
Summary: A facile copper-catalyzed aminosulfonylation method has been developed for the direct synthesis of potentially bioactive 1,3-oxazines using O-homoallyl benzimidates and sodium sulfinates in the presence of tert-butyl peroxybenzoate (TBPB) and XPhos ligand. This method offers the advantages of a cheap catalyst, easily available and stable sulfone reagents, and simple operation.
Article
Chemistry, Organic
Chunxiang Pan, Gaowei Wang, Hengyuan Zhao, Jianxiao Ni, Ruifeng Fan, Yongyun Zhou, Yuanbin Zhu, Shiyuan Wu, Baomin Fan
Summary: An efficient stereoselective cobalt-catalyzed hydrovinylative cyclization of 1,6-enynes with chalcones to obtain functionalized pyrrolidines has been developed. The products were furnished in good yields with up to 93% ee. A plausible mechanism through which the transformation was initiated by cyclization of 1,6-enynes is proposed.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Fu-Sheng He, Yanfang Yao, Zhimei Tang, Wenlin Xie, Jie Wu
Summary: This study describes an efficient copper-catalyzed multicomponent reaction that allows the synthesis of cyanoalkylsulfonylated pyrrolidines under mild conditions. The reaction exhibits a broad substrate scope and high functional group compatibility, forming multiple new bonds in a single step. A plausible mechanism involving a cyanoalkylsulfonyl radical species is proposed based on control experiments.
ORGANIC CHEMISTRY FRONTIERS
(2021)
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
Zhantao Yang, Zhiqiang Yu, Yulin He, Wei Feng, Yinchao Zhang, Junjie Wang, Xiangtao Kong, Chun-Hua Yang
Summary: A Rh-catalyzed regioselective, stereoselective carbocyclization/borylation reaction of acrylate-containing 1,6-enynes was developed, enabling the synthesis of versatile and densely functionalized pyrrolidine compounds. The reaction allows for the formation of pyrrolidines with either (Z) or uncommon (E) geometry at the double bond, depending on the substituent on the alkyne, with sterically hindered and conjugative aryl groups favoring the latter configuration. The reaction also leads to the formation of a tetrasubstituted vinyl boronate, containing an all-carbon quaternary stereocenter.
Article
Chemistry, Organic
Jun-Chen Kang, Zi-Hao Li, Chao Chen, Li-Kun Dong, Shu-Yu Zhang
Summary: This study reports a nickel-catalyzed cascade reductive thiolation of aryl halides with sulfinates driven by paired electrolysis, enabling the synthesis of various thioethers under mild conditions. Mechanistic exploration reveals that a cascade chemical step can occur at the electrode interface and potentially alter the reaction pathway in paired electrolysis, leading to the discovery of novel cascade reactions with unique reactivity.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Biochemistry & Molecular Biology
Hongqiang Dong, Chunli Chen, Jinlei Zhao, Yigang Ji, Wenchao Yang
Summary: The focus of this investigation is a novel approach to synthesize sulfonylated heterocycles, which addresses the limitations of conventional methods by using an affordable sulfonylating agent and operating under metal-free and photocatalyst-free conditions.
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, Multidisciplinary
You-lu Pan, Xiao-meng Gong, Rong-rong Hao, Shen-xin Zeng, Zheng-rong Shen, Wen-hai Huang
Summary: A facile CuBr2 induced radical relay addition/cyclization reaction has been developed for the synthesis of a broad range of sulfonated compounds. Some of the synthesized compounds exhibited bioactivity against cancer cell lines. This protocol offers advantages of low-cost, base-free, simple operation, and broad functional group tolerance.
Article
Chemistry, Organic
Raju Jannapu Reddy, Arram Haritha Kumari, Gamidi Rama Krishna
Summary: A new class of 1,6-enyne-containing propargylic alcohols has been designed and synthesized for the direct synthesis of 3-alkenyl benzoheteroles. The reactions involving Ag-catalyzed cascade radical sulfonylative-cycloannulation and three-component coupling have provided efficient access to a wide range of benzoheterole derivatives. The scalability of the reaction and its compatibility with late-stage synthetic transformations have been successfully demonstrated. A plausible mechanism is proposed based on experimental results and control experiments.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
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, Organic
Undamatla Suri Babu, Maneesh Kumar Reddy Singam, Muniganti Naveen Kumar, Jagadeesh Babu Nanubolu, Maddi Sridhar Reddy
Summary: This article presents a general approach to the synthesis of napthyridinones through the Pd-catalyzed annulation of 1,6-enynes with 2-iodoanilines. The protocol involves a rare carbo-aminative cyclization via the 6-endo-trig mode, and overcomes the commonly observed exo-trig/dig cyclizations. The regioselective aryl palladation of alkyne followed by intramolecular Heck-type reaction enables the cascade synthesis.
Article
Chemistry, Multidisciplinary
Zhengtian Ding, Yiming Wang, Wenfeng Liu, Yate Chen, Wangqing Kong
Summary: The study presents an unprecedented nickel-catalyzed one-pot synthesis of enantioenriched spiroindanones from readily available 1,6-enynes and o-formylarylboronic acids. The reaction proceeds smoothly under redox-neutral conditions, demonstrating excellent regio-, enantio-, and diastereoselectivity with a broad substrate scope.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Organic
Tao Wang, Ji-Xun Guan, Yun-Xuan Tan, Ping Tian
Summary: This paper reports the first cobalt-catalyzed highly selective arylation carbocyclization reaction of 1,6-allenynes with arylboronic acids. The reaction demonstrates moderate to high yields, broad substrate scope, and good compatibility with functional groups.
Article
Chemistry, Organic
Ran Ding, Ming-Hua Mao, Wei-Zhen Jia, Jian-Ming Fu, Lei Liu, Yue-Yuan Mao, Yu Guo, Pei-Long Wang
Summary: A practical method for the radical cyclization of olefinic enamides using sodium sulfinates was reported, leading to the synthesis of a series of sulfonylated pyrrolines and pyrrolinones with wide functional group tolerance, providing convenient access to valuable prochiral pyrroline and pyrrolinone building blocks.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
