111122-85-1Relevant academic research and scientific papers
Rhodium-Catalyzed Site-Selective Coupling of Indoles with Diazo Esters: C4-Alkylation versus C2-Annulation
Chen, Xiaohong,Zheng, Guangfan,Li, Yunyun,Song, Guoyong,Li, Xingwei
, p. 6184 - 6187 (2017)
A Rh(III)-catalyzed site-selective C-H activation of C(3)-functionalized indoles in a coupling with diazo esters has been realized with carbonyl as a weakly coordinating group. The coupling selectivity is dictated by the temperature and additives, affording either C4-alkylated indoles or C2-annulated lactones in moderate to excellent efficiency.
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
, 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.).
Cascade Reaction to Selectively Synthesize Multifunctional Indole Derivatives by IrIII-Catalyzed C?H Activation
Chai, Xin-Yue,Xu, Hui-Bei,Dong, Lin
supporting information, p. 13123 - 13127 (2021/08/13)
An effective and condition-controlled way to synthesize with high selectivity a variety of functionalized indoles with potent biological properties has been developed. Notably, 2,4-dialkynyl indole products were obtained by direct double C?H bond alkynylation, whereas alkynyl at the C4 position could convert to carbonyl to generate 2-alkynyl-3,4-diacetyl indoles fast and effectively. Additionally, a one-pot relay catalytic reaction led to 2,5-di-alkynyl-3,4-diacetyl indoles when using a carbonyl group as the directing group and by controlling the type and quantity of additives. A possible mechanism was proposed based on many studies including deuterium-exchange experiments, the necessary conditions of product conversion, and the effect of water on the reaction.
New Friedel-Crafts strategy for preparing 3-acylindoles
Li, Lian-Hua,Niu, Zhi-Jie,Liang, Yong-Min
supporting information, p. 7792 - 7796 (2018/11/21)
A selective Friedel-Crafts acylation of indoles via an unusual cleavage of the amide C-N bond was achieved by triflic anhydride activation. This method offers rapid efficient access to high-biological-value 3-acylindoles, performs a series of scrupulous mechanistic studies and offers a strong courage that amide synthons can form new C-C bonds under transition-metal-free conditions.
Synthesis of carbonylated heteroaromatic compounds: Via visible-light-driven intramolecular decarboxylative cyclization of o -alkynylated carboxylic acids
Gao, Fei,Wang, Jiu-Tao,Liu, Lin-Lin,Ma, Na,Yang, Chao,Gao, Yuan,Xia, Wujiong
, p. 8533 - 8536 (2017/08/04)
An efficient strategy for the easy access to carbonylated heteroaromatic compounds has been developed via a visible-light-promoted intramolecular decarboxylative cyclization reaction of o-alkynylated carboxylic acids. This method is characterized by its b
Regiocontrolled Direct C?H Arylation of Indoles at the C4 and C5 Positions
Yang, Youqing,Gao, Pan,Zhao, Yue,Shi, Zhuangzhi
supporting information, p. 3966 - 3971 (2017/03/27)
An effective and practical strategy has been established for the direct and site-selective arylation of indoles at the C4 and C5 positions with the aid of a readily accessible, cheap, and removable pivaloyl directing group at the C3 position. This transfo
ZrCl4-mediated regio- and chemoselective friedel-crafts acylation of indole
Guchhait, Sankar K.,Kashyap, Maneesh,Kamble, Harshad
experimental part, p. 4753 - 4758 (2011/07/08)
An efficient method for regio- and chemoselective Friedel-Crafts acylation of indole using acyl chlorides in the presence of ZrCl4 has been discovered. It minimizes/eliminates common competing reactions that occur due to high and multiatom-nucleophilic character of indole. In this method, a wide range of aroyl, heteroaroyl alkenoyl, and alkanoyl chlorides undergo smooth acylation with various indoles without NH protection and afford 3-acylindoles in good to high yields.
2-Substituted 1,3-Benzoxathiolium Tetrafluoroborates as Useful Acylating Agents of Electron-Rich Aromatic and Heteroaromatic Compounds
Cadamuro, Silvano,Degani, Iacopo,Fochi, Rita,Gatti, Antonella,Regondi, Valeria
, p. 311 - 314 (2007/10/02)
2-Substituted 1,3-benzoxathiolium tetrafluoroborates were used for the two-step acylation of electron-rich aromatic and heteroaromatic compounds: 1,3-dimethoxybenzene, 1,3,5-trimethoxybenzene, pyrrole and indoles.In most of the cases intermediate 2,2-disubstituted 1,3-benzoxathioles were obtained in good to high yields (55-100percent) and subsequent hydrolysis of these with mercury(II) oxide and aqueous tetrafluoroboric acid (35percent) in tetrahydrofuran afforded the corresponding ketones in almost quantitative yields.
