79554-84-0Relevant articles and documents
Transition-metal-free synthesis of vicinal triborated compounds and selective functionalisation of the internal C-B bond
Davenport, Elliot,Fernandez, Elena
, p. 10104 - 10107 (2018)
1,2,3-Triborated compounds can be prepared by simple nucleophilic borylation of 1,3-dienes, without the assistance of metal catalysts. Selective functionalisation of the internal C-B bond of the 1,2,3-triborated compounds, through cross-coupling with aryl
Ni-Catalyzed Regioselective Hydroarylation of 1-Aryl-1,3-Butadienes with Aryl Halides
Wang, Chengdong,Guo, Yingjie,Wang, Xiaoming,Wang, Zheng,Ding, Kuiling
supporting information, p. 15903 - 15907 (2021/10/07)
An efficient nickel-catalyzed regioselective hydroarylation of 1,3-dienes with aryl halides and a silane has been developed, affording a range of allylic arenes in good to excellent yields under mild conditions. This method exhibits broad substrate scope,
Palladium-Catalyzed Asymmetric Tandem Denitrogenative Heck/Tsuji-Trost of Benzotriazoles with 1,3-Dienes
Li, Yin-Lin,Wu, Hai-Hong,Zhang, Junliang,Zhang, Pei-Chao
supporting information, p. 13010 - 13015 (2021/09/07)
The asymmetric denitrogenative cycloaddition has emerged as a powerful tool to build chiral aza-heterocyles. However, only one example of asymmetric denitrogenative cycloaddition of benzotriazole with unsaturated hydrocarbons has been explored so far, bec
Asymmetric Counteranion Directed Catalytic Heck/Tsuji-Trost Annulation of Aryl Iodides and 1,3-Dienes
Xu, Jia-Cheng,Yin, Yi-Zhuo,Han, Zhi-Yong
supporting information, p. 3834 - 3838 (2021/05/26)
A chiral anion-mediated asymmetric Heck/Tsuji-Trost reaction of aryl iodides and 1,3-dienes is presented. Chiral indoline derivatives could be afforded with remarkably higher yields and enantioselectivities than our previous chiral ligand-based method. Silver carbonate is employed as both base and halide scavenger to ensure fast and recyclable exchange of the catalytic amount of chiral anions. Fast salt metathesis, as well as the acceleration effect of the chiral anion, could both benefit the stereocontrol of the reaction.
Stereoselective and Atom-Economic Alkenyl C-H Allylation/Alkenylation in Aqueous Media by Iridium Catalysis
Ding, Liyuan,Huang, Yinhua,Lu, Xiunan,Shen, Wenzhou,Xu, Liangyao,Yu, Feifei,Zhang, Jian,Zhong, Guofu,Zhong, Liangjun
, p. 7225 - 7237 (2020/07/07)
A practical and atom-economic protocol for the stereoselective preparation of various 1,4-and 1,3-diene skeletons through iridium-catalyzed directed olefinic C-H allylation and alkenylation of NH-Ts acrylamides in water was developed. This reaction tolerated a wide scope of substrates under simple reaction conditions and enabled successful gram-scale preparation. Furthermore, an asymmetric variant of this reaction giving enantioenriched 1,4-dienes was achieved employing a chiral diene-iridium complex as the catalyst.
In-chain functionalized syndiotactic 1,2-polybutadiene by a Ziegler-Natta iron(III) catalytic system
Liang, Shanshan,Zhang, Huaqiang,Cong, Rixin,Liu, Heng,Wang, Feng,Hu, Yanming,Zhang, Xuequan
, p. 33465 - 33471 (2019/10/28)
Copolymerization of 1,3-butadiene with four 1-substituted 1,3-diene comonomers bearing amino and alkyoxy groups by a Ziegler-Natta iron(iii) catalytic system to access in-chain functionalized syndiotactic 1,2-polybutadiene is reported herein. The polar co
Iron(III)/O2-Mediated Regioselective Oxidative Cleavage of 1-Arylbutadienes to Cinnamaldehydes
Bhowmik, Amit,Fernandes, Rodney A.
supporting information, p. 9203 - 9207 (2019/11/14)
A simple, efficient, and environmentally benevolent regioselective oxidative cleavage of 1-arylbutadienes to cinnamaldehydes mediated by iron(III) sulfate/O2 has been developed. The reaction offered good yields and excellent regioselectivity and showed good functional group tolerance (31 examples). The method is important, as few reports with limited substrate scope are available for such excellent oxidative cleavage of conjugated dienes.
Iridium-catalyzed alkenyl C-H allylation using conjugated dienes
Xu, Liangyao,Meng, Keke,Zhang, Jian,Sun, Yaling,Lu, Xiunan,Li, Tingyan,Jiang, Yan,Zhong, Guofu
supporting information, p. 9757 - 9760 (2019/08/20)
An iridium-catalyzed C-H allylation of acrylamides with conjugated dienes was developed, using NH-Ts amide as the directing group. The ligand- and additive-free protocol provided a convenient and atom economic synthesis of branched 1,4-diene skeletons, enabling the tolerance of a wide scope of functionalities such as OMe, F, Cl, Br and CF3. The utility of this protocol is also demonstrated by a preparative scale, as well as C-H functionalization of artemisic amide. Furthermore, NH-Ts amide was efficiently removed by methylation and hydrolysis procedures to provide 1,4-dienoic acid.
Highly-functionalized arene synthesis based on palladium on carbon-catalyzed aqueous dehydrogenation of cyclohexadienes and cyclohexenes
Yasukawa, Naoki,Yokoyama, Hiroki,Masuda, Masahiro,Monguchi, Yasunari,Sajiki, Hironao,Sawama, Yoshinari
supporting information, p. 1213 - 1217 (2018/03/28)
Transition metal-catalyzed dehydrogenation is a clean oxidation method requiring no additional oxidants. We have accomplished a heterogeneous Pd/C-catalyzed aqueous dehydrogenation of 1,4-cyclohexadienes and cyclohexenes to give the corresponding highly-functionalized arenes. Furthermore, various arenes could be efficiently constructed in a one-pot manner via a Diels-Alder reaction and the following dehydrogenation.
Copper-Catalyzed Dehydrogenative Diels-Alder Reaction
Jiang, Bing,Liang, Qiu-Ju,Han, Yu,Zhao, Meng,Xu, Yun-He,Loh, Teck-Peng
supporting information, p. 3215 - 3219 (2018/06/11)
A practical and effective copper-catalyzed dehydrogenative Diels-Alder reaction of gem-diesters and ketone with dienes has been established. The active dienophiles were generated in situ via a radical-based dehydrogenation process, which reacted with a wide variety of dienes to afford various polysubstituted cyclohexene derivatives in good to excellent yields.
