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
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, Physical
Yulong Song, Chunling Fu, Shengming Ma
Summary: A copper-catalyzed three-component reaction has been developed for the synthesis of 1,7-double-functionalized allenes, which are difficult to prepare. The allenyl nitrile products demonstrate their potential as platform molecules in synthesis.
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
Yinchao Zhang, Wenxiu Xu, Tongtong Gao, Mengjuan Guo, Chun-Hua Yang, Hua Xie, Xiangtao Kong, Zhantao Yang, Junbiao Chang
Summary: A Pd-catalyzed borylsilylative cyclization of 1,6-allenynes with PhMe2SiBpin was developed, providing a practical and general method to synthesize carbocycles and heterocycles bearing silyl and boryl groups with high regioselectivities and stereoselectivities.
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, Organic
Wen-Zhe Ji, Hao-Nan Shi, Wen-Juan Hao, Ping Wei, Shu-Jiang Tu, Bo Jiang
Summary: A new three-component strategy has been developed for the synthesis of stereodefined (Z)-3,4-dihydronaphthalen-1(2H)-ones through copper-catalyzed annulation-cyanotrifluoromethylation. The reaction shows high yields and complete stereoselectivity, making it a promising method for the rapid synthesis of these compounds.
TETRAHEDRON LETTERS
(2021)
Article
Chemistry, Physical
Yu-Fei Fu, Xiao-Jun Liu, De-Zhan Chen, Jian-Biao Liu
Summary: In this study, a computational mechanistic investigation of the cobalt-catalyzed hydroboration/cyclization reaction of 1,6-enynes was conducted. The role of ligand coordination on the mechanism and regioselectivity was explored. The results showed that steric repulsions and hydrogen bonding interactions between the substrate and the ligand played important roles in controlling the competing migration insertion. Energy decomposition analyses revealed the impact of steric and electronic effects on regioselectivity, with electrostatics and orbital interactions being the dominant factors.
JOURNAL OF CATALYSIS
(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
Linglong Ding, Yi-Hui Deng, Tian-Yu Sun, Dawei Wang, Yun-Dong Wu, Xiao-Feng Xia
Summary: Through the control by functional groups, a catalytic divergent cycloisomerization of 1,6-enynes was achieved using a combination of a Pd(0) catalyst with glucose for the synthesis of pyrrole, cyclopentene, and tetra-hydropyridine derivatives. Detailed DFT calculations have provided evidence for the different pathways of selective cyclization/isomerization.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Applied
Yunhe Lv, Jinhui Xie, Weiya Pu, Xue Wang, Huanhuan Zhang, Xuerui Li, Yan Liu, Fei Chen, Yunfeng Xu
Summary: We developed a strategy for the copper-catalyzed three-component reaction to synthesize tetrasubstituted allenes with phosphinoyl and cyano groups. The reaction exhibited high functional group compatibility and good yields under mild conditions. A preliminary reaction mechanism involving the formation of phosphinoyl radicals and their regioselective addition to 1,3-enynes was proposed.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
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
Shaoqun Zhu, Yuejie Sun, Yingjie Pan, Xiaoyun Chen, Huaguang Yu, Ying Han, Chaoguo Yan, Yaocheng Shi, Hong Hou
Summary: In this study, a novel hydroalkylative cyclization method was developed using visible-light photoredox catalysis, resulting in the synthesis of various alkenyl heterocyclic compounds.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Dachang Bai, Ruoshi Cheng, Jiaxin Yang, Wenjie Xu, Xingge Chen, Junbiao Chang
Summary: Transition-metal-catalyzed hydrosilylation is an efficient strategy for the synthesis of valuable organosilanes, while divergent synthetic routes are still a challenge.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Fei Hou, Yingtang Ning, Lili Song, Zequn Tan, Jiawen Yang, Zhigang Liu, Fen-Er Chen
Summary: A rhodium-catalyzed enantioselective hydroboration/cyclization reaction of 1,6-enynes using a spirosiladiphosphine ligand has been achieved. The reaction allows the synthesis of five-membered hetero- and carbocycles bearing a boron handle with high activity and selectivity. Various enynes and organoboranes have been successfully utilized, including enynes containing terminal alkynes for the first time. The high yields and selectivities highlight the synthetic utility of these novel spirosiladiphosphine ligands.
Article
Chemistry, Applied
Yu-Tao He, Qiang Wang, Jiahui Zhao, Xiao-Zhen Wang, Yi-Feng Qiu, Yu-Chen Yang, Jing-Yuan Hu, Xue-Yuan Liu, Yong-Min Liang
ADVANCED SYNTHESIS & CATALYSIS
(2015)
Article
Chemistry, Multidisciplinary
Yu-Tao He, Qiang Wang, Jiahui Zhao, Xue-Yuan Liu, Peng-Fei Xu, Yong-Min Liang
CHEMICAL COMMUNICATIONS
(2015)
Article
Chemistry, Organic
Yu-Tao He, Qiang Wang, Lian-Hua Li, Xue-Yuan Liu, Peng-Fei Xu, Yong-Min Liang
Article
Chemistry, Organic
Yu-Qi Wang, Yu-Tao He, Lu-Lu Zhang, Xin-Xing Wu, Xue-Yuan Liu, Yong-Min Liang
Article
Chemistry, Organic
Yu-Tao He, Lian-Hua Li, Qiang Wang, Wangsuo Wu, Yong-Min Liang
Article
Chemistry, Multidisciplinary
Yu-Tao He, Lian-Hua Li, Yan-Fang Yang, Yu-Qi Wang, Jian-Yi Luo, Xue-Yuan Liu, Yong-Min Liang
CHEMICAL COMMUNICATIONS
(2013)
Article
Chemistry, Organic
Yu-Tao He, Lian-Hua Li, Yan-Fang Yang, Zhao-Zhao Zhou, Hui-Liang Hua, Xue-Yuan Liu, Yong-Min Liang
Article
Chemistry, Organic
Yu-Tao He, Joonghee Won, Jiyun Kim, Bohyun Park, Taehwan Kim, Mu-Hyun Baik, Sungwoo Hong
ORGANIC CHEMISTRY FRONTIERS
(2018)
Article
Chemistry, Multidisciplinary
Yu Chen, Guang-Yi Zhang, Chan Guo, Ping Lan, Martin G. Banwell, Yu-Tao He
Summary: The silver-promoted reaction allows for the efficient synthesis of C2-substituted pyridines by ring-opening of tertiary cyclobutanols and addition to N-methoxypyridinium salts. A wide range of cyclobutanols and pyridinium salts are compatible with the reaction conditions.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Organic
Ting-Ting Yuan, Jing Chen, Le Nhan Pham, Sayan Paul, Lorenzo V. White, Jialong Li, Ping Lan, Michelle L. Coote, Martin G. Banwell, Yu-Tao He
Summary: Efficient and versatile syntheses of methylene-bridged bis-heterocycles are described, which involve a visible light-mediated radical-relay sequence. This process begins with the homolysis of O-H bonds contained within & beta;,& gamma;-unsaturated oximes, generating oxygen-centred radicals that add to the tethered olefin. The resulting carbon-centered radical is then trapped by an added N-heteroarenium salt. These findings provide new insights into alkoxy radical-mediated transformations and access to new molecular scaffolds with potential applications in various settings.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Multidisciplinary
Yu-Tao He, Dahye Kang, Inwon Kim, Sungwoo Hong
