17017-58-2Relevant academic research and scientific papers
Palladium-catalysed intramolecular annulation of 2-haloanilines and ketones: Enolate arylation vs. nucleophilic addition to the carbonyl group
Sole,Vallverdu,Peidro,Bonjoch
, p. 1888 - 1889 (2001)
Two alternative annulation pathways involving either the enolate arylation or the addition to the ketone carbonyl group can operate in the Pd-catalysed intramolecular coupling of 2-haloanilines and ketones.
Synthesis of bisindolylmethane, bispyrrolylmethane, and indolylpyrrolylmethane derivatives via reductive heteroarylation
Zhou, Hang,Huang, Zhuo,Huang, He,Song, Chuanjun,Chang, Junbiao
, (2021)
An efficient and general reductive heteroarylation approach toward the synthesis of bisindolylmethane, bispyrrolylmethane, and indolylpyrrolylmethane derivatives has been developed. Thus, treatment of acylpyrrole or acylindole derivatives with indoles or pyrroles in the presence of a combination of sodium borohydride and acetic acid resulted in the formation of the title compounds in moderate to excellent isolated yields.
Solid-State Radical C?H Trifluoromethylation Reactions Using Ball Milling and Piezoelectric Materials
Ito, Hajime,Kubota, Koji,Lee, Joo Won,Pang, Yadong
supporting information, p. 22570 - 22576 (2020/10/21)
The application of piezoelectricity for the generation of trifluoromethyl (CF3) radicals is reported together with the development of a method for the mechanochemical C?H trifluoromethylation of aromatic compounds. As compared to conventional solution-based approaches, this mechanoredox C?H trifluoromethylation enables cleaner and more sustainable access to a wide range of trifluoromethylated N-heterocycles and peptides, which are important structural motifs in modern drug discovery. This study thus represents an important milestone for future applications of mechanoredox systems to medicinal and pharmaceutical science.
Synthesis of Pyrido[2,3-b]indole Derivatives via Rhodium-Catalyzed Cyclization of Indoles and 1-Sulfonyl-1,2,3-triazoles
An, Yuehui,Chen, Yidian,Duan, Shengguo,Li, Chuan-Ying,Xu, Ze-Feng,Xue, Bing,Zhang, Wan
supporting information, (2020/04/22)
Acyloxy-substituted α,β-unsaturated imines generated in situ from triazoles can act as aza-[4 C] synthons and be trapped by indoles in a stepwise [4 + 2] cycloaddition reaction, thus providing rapid access to valuable pyrido[2,3-b]indoles in high yields. Attractive features of this reaction system include operational simplicity, readily available substrates, construction of sterically demanding quaternary centers, and convenient derivatization using triflate. (Figure presented.).
Room-Temperature Palladium(II)-Catalyzed Direct 2-Arylation of Indoles with Tetraarylstannanes
Liu, Yuxia,Wang, Chao,Huang, Linjuan,Xue, Dong
supporting information, p. 1613 - 1618 (2020/09/15)
A palladium(II)-catalyzed direct 2-arylation of indoles by tetraarylstannanes with oxygen (balloon) as the oxidant at room temperature has been developed. Various tetraarylstannanes can be employed as aryl sources for 2-arylation of indoles in up to 89% yield, providing a practical and efficient catalytic protocol for accessing 2-arylindoles.
The palladium-catalyzed direct C3-cyanation of indoles using acetonitrile as the cyanide source
Feng, Kejun,Li, Qiang,Li, Yuanhua,Liu, Bifu,Liu, Min,Zhou, Yongbo
supporting information, p. 6108 - 6114 (2020/10/21)
The ligand-free palladium-catalyzed C3-cyanation of indoles via direct C-H functionalization was achieved. This protocol, utilizing CH3CN as a green and readily available cyanide source, produced the desired products in moderate to good yields through transition-metal-catalyzed C-CN bond cleavage. This journal is
Reductive aromatization of oxindoles to 3-substituted indoles
Mandal, Tirtha,Chakraborti, Gargi,Dash, Jyotirmayee
, (2020/06/21)
A practical and scalable approach for the synthesis of 3-substituted indoles is delineated via hydride nucleophilic addition to 3-substituted-2-oxindoles. The reaction proceeds through reductive aromatization involving indolinium ion intermediate. A wide range of 3-functionalized indoles have been synthesized. The method is employed for the synthesis of 3,3?-bis-indoles and a dimeric 3-indole derivative. Moreover, this protocol is used to obtain naturally occuring amino acid tryptamine.
Nickel-Catalyzed Mizoroki-Heck/Amination Cascade Reactions of o-Dihaloarenes with Allylamines: Synthesis of Indoles
Chen, Xu,Lin, Jin,Wang, Biao,Tian, Xu
supporting information, p. 7704 - 7708 (2020/10/12)
An efficient Mizoroki-Heck/amination cascade reaction of o-dihaloarenes with allylamines has been developed using nickel and IPr carbene ligand as catalyst. This protocol enables the synthesis of a broad range of substituted indoles by a cascade process, from readily available starting materials. Mechanistic studies suggest that the Mizoroki-Heck reaction occurred first under IPr-nickel catalysis.
B(C6F5)3-Catalyzed Direct C3 Alkylation of Indoles and Oxindoles
Basak, Shyam,Alvarez-Montoya, Ana,Winfrey, Laura,Melen, Rebecca L.,Morrill, Louis C.,Pulis, Alexander P.
, p. 4835 - 4840 (2020/04/22)
The direct C3 alkylation of indoles and oxindoles is a challenging transformation, and only a few direct methods exist. Utilizing the underexplored ability of triaryl boranes to mediate the heterolytic cleavage of α-nitrogen C-H bonds in amines, we have developed a catalytic approach for the direct C3 alkylation of a wide range of indoles and oxindoles using amine-based alkylating agents. We also employed this borane-catalyzed strategy in an alkylation-ring opening cascade.
Tandem C-H Transformations by a Single Iridium Catalyst: Direct Access to Indoles and Indolines from o-Alkyl-N-methylanilines
Ohmura, Toshimichi,Yagi, Kaito,Kusaka, Satoshi,Suginome, Michinori
, p. 3152 - 3157 (2020/03/04)
In the presence of an iridium catalyst bearing DTBM-SEGPHOS as a ligand and tert-butylethylene as a hydrogen scavenger, 2-ethyl-N-methylanilines were converted directly to 3-methylindoles in high yields. The reaction proceeded efficiently in mesitylene at 150 °C through transfer dehydrogenation of the ethyl group and following intramolecular dehydrogenative C-H/C-H coupling of the N-methyl group with the vinyl group formed in situ. The iridium catalyst system was applied to the asymmetric conversion affording enantioenriched indolines bearing a quaternary stereogenic carbon center at the C3 position.
