441715-92-0Relevant articles and documents
Rhodium(III)-Catalyzed Regioselective C?H Allylation and Prenylation of Indoles at C4-Position
Zhang, Shang-Shi,Liu, Yan-Zhi,Zheng, Yi-Chuan,Xie, Hui,Chen, Shao-Yong,Song, Jia-Lin,Shu, Bing
supporting information, p. 64 - 70 (2021/11/03)
Herein, Rh(III)-catalyzed C4-selective C?H allylation and prenylation of indoles by using a weak carbonyl coordination directing group have been reported. By employing 5-methylene-1,3-dioxan-2-ones, 4-vinyl-1,3-dioxolan-2-ones and 2-methyl-2,3-butadiene as scalable cross-coupling partners, these divergent synthesis protocols proceed smoothly under redox-neutral reaction conditions, delivering various allylated and prenylated indoles in moderate to satisfied yields. This transformation exhibits high functional-groups compatibility and broad substrate scope. Scale-up experiment and mechanistic studies were also accomplished. (Figure presented.).
Copper-Catalyzed Synthesis of Indolyl Benzo[b]carbazoles and Their Photoluminescence Property
Hao, Tonggang,Huang, Long,Wei, Yin,Shi, Min
supporting information, p. 5133 - 5137 (2021/07/19)
A copper-catalyzed cascade cyclization of dihydroisobenzofurans with indoles for the rapid construction of indoly benzo[b]carbazoles has been reported, providing the desired products in moderate to good yields under mild conditions along with a broad substrate scope and good functional group tolerance. The photoluminescence property of these indoly benzo[b]carbazoles has also been investigated.
Assembly of polycyclic N-heterocycles: Via copper-catalyzed cycloamination of indolylquinones and aromatic amines
Dong, Yu,Mei, Ting,Ye, Ji-Xian,Chen, Xiang-Long,Jiang, Hui,Chang, Bo,Wang, Zhi-Fan,Shi, Zhi-Chuan,Li, Zhong-Hui,He, Bing
supporting information, p. 4593 - 4598 (2021/05/31)
The copper-catalyzed cycloamination of indolylquinones and various (hetero)aromatic amines under ligand-free conditions for the synthesis of polycyclic N-heterocycles has been developed. This method allows facile access to polycyclic N-heterocycles with the tolerance of chloride, bromide, amino, thio, etc. groups in moderate to high yields (60-89%).
Salicylaldehyde-Promoted Cobalt-Catalyzed C-H/N-H Annulation of Indolyl Amides with Alkynes: Direct Synthesis of a 5-HT3 Receptor Antagonist Analogue
Huang, Mao-Gui,Shi, Shuai,Li, Ming,Liu, Yue-Jin,Liu, Yue-Jin
supporting information, p. 7094 - 7099 (2021/09/14)
A cobalt-catalyzed annulation of the C(sp2)-H/N-H bond of indoloamides with alkynes assisted by 8-aminoquinoline is reported for the synthesis of six-membered indololactams. The use of salicylaldehyde as the ligand is crucial for this transformation. The protocol has a broad scope for both alkynes and indoles. Preparing an active Co complex illustrates that salicylaldehyde plays a key role in the C-H activation step. The synthetic applications are proven by the gram-scale reaction and one-step construction of the multicyclic 5-HT3 receptor antagonist.
Synthesis of 3-halogenated 2,3′-biindoles by a copper-mediated 2,3-difunctionalization of indoles
Gu, Xiaoting,Liang, Taoyuan,Wei, Wanxing,Zhang, Xiaoxiang,Zhang, Yingying,Zhang, Zhuan
supporting information, p. 10403 - 10407 (2021/12/17)
A copper-mediated 2,3-difunctionalization of indoles to afford 3-halogenated 2,3′-biindoles is described herein. The protocol uses readily available feedstocks and a naturally abundant copper catalyst system, which allows the regioselective formation of C-C and C-X (X = Cl & Br) bonds in one single operation. Here the copper metal salt serves not only as a catalyst but also as a reactant to provide the source of halogen. This operationally simple procedure avoids the utilization of environmentally unfriendly reagents and displays good functional group compatibility. Noteworthily, the introduction of halogen into molecules would offer great potential for further chemical transformations. This journal is
Sulfoxide-Promoted Chlorination of Indoles and Electron-Rich Arenes with Chlorine as Nucleophile
Ji, Yuan-Zhao,Li, Hui-Jing,Wang, Yi-Ruo,Wu, Yan-Chao,Zhang, Zheng-Yan
supporting information, (2020/02/05)
An efficient chlorination of indoles and electron-rich arenes with chlorine anion as nucleophile is described. With the use of ethyl phenyl sulfoxide as the promoter, the reaction went smoothly under metal-free and mild conditions. Various indoles and electron-rich arenes are converted into the corresponding chlorinated compounds in moderate to excellent yields. A plausible interrupted Pummerer reaction mechanism was proposed without the oxidation of chloride anion. In addition, the byproduct thioether could be easily converted to the starting material sulfoxide just by a simple oxidation reaction. (Figure presented.).
Isothiourea-Catalyzed Enantioselective Synthesis of Tetrahydro-α-carbolinones
Liu, Honglei,Slawin, Alexandra M. Z.,Smith, Andrew D.
supporting information, p. 1301 - 1305 (2020/02/25)
An isothiourea-catalyzed enantioselective annulation protocol using indolin-2-imines with a series of α,β-unsaturated p-nitrophenyl esters for the synthesis of tetrahydro-α-carbolinones was developed. Using 5 mol % of the isothiourea HyperBTM as the Lewis base catalyst, this process allows the enantioselective preparation of a range of C(4)-substituted tetrahydro-α-carbolinones in good to excellent yield and with high enantioselectivity (20 examples, 32-99% yield and up to 99:1 er).
Isodesmic C-H Borylation: Perspectives and Proof of Concept of Transfer Borylation Catalysis
Rochette, étienne,Desrosiers, Vincent,Soltani, Yashar,Fontaine, Frédéric-Georges
supporting information, p. 12305 - 12311 (2019/08/20)
The potential advantages of using arylboronic esters as boron sources in C-H borylation are discussed. The concept is showcased using commercially available 2-mercaptopyridine as a metal-free catalyst for the transfer borylation of heteroarenes using arylboronates as borylation agents. The catalysis shows a unique functional group tolerance among C-H borylation reactions, tolerating notably terminal alkene and alkyne functional groups. The mechanistic investigation is also described.
Switchable regioselection of C-H thiolation of indoles using different TMS counterions
Ji, Yuan-Zhao,Li, Hui-Jing,Zhang, Jin-Yu,Wu, Yan-Chao
supporting information, p. 11864 - 11867 (2019/10/11)
A switchable regioselectivity in C-H thiolation reaction by simply swapping the counteranions of TMS is reported here for the first time. An exclusive C3-H thiolation of indoles with sodium arylsulfinates was achieved in the presence of TMSCl as a promoter. In contrast, with the use of TMSOTf instead of TMSCl under otherwise identical conditions, a regiospecific C2-H thiolation of indoles was realized with the same set of substrates.
Metal-free synthesis of benzimidazo[1,2-c]quinazolin-6-ones with indole and benzenediamine oxidized by I2/TBHP
Dai, Zhen,Li, Songhua,Li, Yunyi,Feng, Lei,Ma, Chen
supporting information, p. 2012 - 2017 (2019/02/20)
A variety of benzimidazo[1,2-c]quinazolin-6-ones derivatives can be accessed in moderate to good yields under simple and metal-free reaction conditions using indoles and o-benzenediamines oxidized by iodine and TBHP. This procedure works in reasonable yields for different indoles as well as o-benzenediamines thus may provide a good synthesis of quinazolinones. A TBHP oxidized ring expansion reaction mechanism that explains the synthesis of benzimidazo[1,2-c]quinazolin-6-ones were reported.
