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
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
Rattana Worayuthakarn, Sirikan Deesiri, Kittipong Chainok, Nanthawat Wannarit, Somsak Ruchirawat, Nopporn Thasana
Summary: A highly regioselective divergent approach for synthesizing phosphine-containing indane/indene derivatives from ene-yne-oxazolone precursors was reported, along with proposed reaction mechanism. The protocol utilized H-phosphonate as reagent in a silver-catalyzed or base-mediated cyclization to construct the corresponding compounds in good yields (up to 88%).
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Applied
Chada Raji Reddy, Roshan Chandrakant Kajare, Nagender Punna
Summary: Herein, we report the synthesis of functionalized dihydro-benzo[b]fluorenones through a manganese-mediated cascade radical cyclization method. The method features high atom- and step-economy, and allows for the construction of three new C-C bonds with high yields under mild reaction conditions, demonstrating the synthetic efficacy of the developed method.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Multidisciplinary
Shi-Ping Wu, Dong-Kai Wang, Qing-Qing Kang, Guo-Ping Ge, Hongxing Zheng, Meiling Zhu, Ting Li, Jun-Qi Zhang, Wen-Ting Wei
Summary: This novel synthetic protocol utilizes a sulfonyl radical to trigger selective iodosulfonylation and bicyclization of 1,6-dienes, demonstrating high selectivity and efficiency, mild reaction conditions, excellent functional group compatibility, and broad substrate scope. It provides a unique platform for precise radical cyclization.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Multidisciplinary
Lin-Ping Hu, De-Run Zhang, Xiao-Hong Huang, Feng-Lin Liu, Xia Li, Ming-Yu Teng, Guo-Li Huang
Summary: The method involves the aryl sulfonyl radical-triggered cascade cyclization of phenyl-linked 1,6-enynes to synthesize biologically important indenes containing alkenyl C-X bonds and 10a,11-dihydro-10H-benzo[b]fluorines. Three new chemical bonds, including C-S, C-C, and C-X bonds, and three C-C bonds are formed in one step. The metal-free, mild reaction conditions, broad substrate scope, and good functional group tolerance make the method attractive and valuable.
CHINESE JOURNAL OF CHEMISTRY
(2022)
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, 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, Multidisciplinary
Yuling Lu, Chunmei Chen, Hucheng Zhu, Zengwei Luo, Yonghui Zhang
Summary: A green and efficient method for the preparation of valuable di-iodinated succinimide derivatives without using any additives has been successfully developed through iodine radical-initiated cascade cyclization. This method is highly atom- and time-economical, with good to excellent yields, and has excellent functional group compatibility. It is also safe to operate and easy to scale up.
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
Ming Dong, Danfeng Wang, Xiaofeng Tong
Summary: The dihalogenative cyclization of 1,6-enyne with the assistance of PhI(OAc)(2) and lithium halide follows a plausible radical mechanism, with the resulting pyrrolidine products containing alkyl- and alkenyl-halide groups that are demonstrated to be suitable for further transformations.
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.
