138343-89-2Relevant academic research and scientific papers
Palladium-catalyzed cross-coupling reactions of 2-indolyldimethylsilanols with substituted aryl halides
Denmark, Scott E.,Baird, John D.
, p. 3649 - 3652 (2004)
(Chemical Equation Presented) A mild and general cross-coupling reaction of 2-indolylsilanols has been developed. The experimental variables that lead to successful coupling are (1) the use of sodium terf-butoxide as the activator, (2) the use of copper(l) iodide in stoichiometric quantities, and (3) the use of Pd2-(dba)3·CHCl3 as the catalyst. Under these conditions N-(Boc)-2-indolyldimethylsilanol reacts with a variety of aromatic iodides to afford the coupling products in good yield (70-84%).
DMSO/SOCl2-mediated C(sp2)-H amination: Switchable synthesis of 3-unsubstituted indole and 3-methylthioindole derivatives
Zhang, Jingran,Li, Xiaoxian,Li, Xuemin,Shi, Haofeng,Sun, Fengxia,Du, Yunfei
supporting information, p. 460 - 463 (2021/01/25)
The reaction of 2-alkenylanilines with SOCl2 in DMSO was found to selectively afford 3-unsubstituted indoles and 3-methylthioindoles. This switchable approach was found to be temperature-dependent: at room temperature, the reaction afforded 3-unsubstituted indoles through intramolecular cyclization and elimination; while at higher temperature, the reaction gave 3-methylthioindoles via further electrophilic methylthiolation.
Nickel-Catalyzed Dearomative Arylboration of Indoles: Regioselective Synthesis of C2- And C3-Borylated Indolines
Brown, M. Kevin,Crook, Phillip F.,Kuniyil, Rositha,Liu, Peng,Trammel, Grace L.
supporting information, p. 16502 - 16511 (2021/10/20)
Indole dearomatization is an important strategy to access indolines: a motif present in a variety of natural products and biologically active molecules. Herein, a method for transition-metal catalyzed regioselective dearomative arylboration of indoles to
Mechanochemical Pd(II)-Catalyzed Direct and C-2-Selective Arylation of Indoles
Das, Dharmendra,Bhutia, Zigmee T.,Chatterjee, Amrita,Banerjee, Mainak
, p. 10764 - 10774 (2019/09/09)
A mechanochemical method for the preparation of synthetically useful 2-arylindoles is developed using Pd(II) as the catalyst in the absence of phosphine ligands in a ball-mill. The developed protocol is highly C-2 selective and tolerant of structural variations with electron-rich and electron-deficient substituents both in indoles and iodoarenes. Arylation is possible in both unprotected indoles and N-protected indoles with the electron-donating group with the former substrate being relatively slower to react and little less yielding. Indoles with a deactivated five-membered ring could also take part in the reaction with ease. The scalability of the reaction was demonstrated by conducting the reaction in the gram scale. In general, the reactions were achieved in a shorter time than the conventional methods.
Organic blue light-emitting fluorescence material based on indole derivative, and blue light-emitting device
-
Paragraph 0046-0050, (2019/11/25)
The invention discloses an organic blue light-emitting fluorescence material based on an indole derivative, and a blue light-emitting device. The organic blue light-emitting fluorescence material comprises a D-A structure, the D is an electron donor, the
Synthesis of indoles from aroyloxycarbamates with alkynes: Via decarboxylation/cyclization
Ma, Nuannuan,Li, Peihe,Wang, Zheng,Dai, Qipu,Hu, Changwen
, p. 2421 - 2426 (2018/04/12)
An efficient Pd-catalyzed decarboxylation/cyclization of aroyloxycarbamates to realize substituted indoles has been disclosed. Terminal alkynes as the coupling partners lead to site specific 2-substituted indoles through two pathways, while internal alkynes with aroyloxycarbamates can be transformed to 2,3-disubstituted indoles directly. This protocol is further demonstrated by the efficient synthesis of indoles as well as the success of employing inexpensive aryl acids as starting materials to construct C-N bonds by releasing CO2.
PtCl4-catalyzed cyclization of N-acetyl-2-alkynylanilines: A mild and efficient synthesis of N-acetyl-2-substituted indoles
Chaisan, Nattawadee,Kaewsri, Wilailak,Thongsornkleeb, Charnsak,Tummatorn, Jumreang,Ruchirawat, Somsak
supporting information, p. 675 - 680 (2018/01/18)
An efficient synthesis of N-acetyl-2-substituted indole derivatives via direct intramolecular hydroamination of N-acetyl-2-alkynylaniline derivatives was developed. The reaction could be applied to a wide range of substrates employing only 1–2 mol% of PtCl4 as the catalyst to furnish the desired indole products in moderate to excellent yields. The current protocol is efficient, reliable and scalable, and could serve as an important tool for convenient and rapid access to this important class of N-heterocyclic skeleton from readily available substrates.
Regioselective Synthesis of 2-Vinylanilines Using O-aroyloxycarba-mates by Sequential Decarboxylation/Amination/Heck Reaction
Li, Peihe,Ma, Nuannuan,Li, Jikun,Wang, Zheng,Dai, Qipu,Hu, Changwen
, p. 8251 - 8257 (2017/08/14)
A new sequential approach for 2-vinylanilines utilizing aryl carboxylic acids as stable, inexpensive and widely available arylating reagents is described. Employing a Pd-POVs catalyst system, this protocol is not only overcoming the restriction barrier of decarboxylative coupling to ortho-substituted substrates, but also provides site-special to create new C(sp2)-N and C(sp2)-C(sp2) bonds. Mechanistic experiments suggest the cleavage of C(sp2)-COOH gives priority to C(sp2)-X bond in this reaction.
Method for preparing indole derivative from carboxylate through palladium catalysis
-
, (2018/01/11)
The invention discloses a method for preparing an indole derivative from carboxylate through palladium catalysis, and belongs to the field of organic methodology. The method comprises (1) reacting aromatic carboxylic acid with a hydroxylamine compound to generate carboxylate, reacting carboxylate with monosubstituted alkyne, and carrying out a series of cascade reaction steps including decarboxylation and coupling to generate a 2-substituted indole compound; and (2) reacting carboxylate with di-substituted alkyne, and carrying out a series of cascade reaction steps including decarboxylation, coupling and cyclization to generate a 2,3-di-substituted indole compound. In the method, the carboxylic acid raw material is cheap and available, so that the production cost is reduced. The method is mild in experimental condition and good in substrate universality. Through multi-step cascade reaction, the reaction intermediate doesn't require separation. The method is simplified in operation steps and can be used for enterprise production.
Palladium on Layered Double Hydroxide: A Heterogeneous System for the Enol Phosphate Carbon-Oxygen Bond Activation in Aqueous Media
Senra, Jaqueline D.,Silva, Aires C.,Santos, Raquel V.,Malta, Luiz Fernando B.,Simas, Alessandro B. C.
, (2017/02/05)
In this work, a new catalytic approach for the C-O activation of enol phosphates based on a palladium supported on layered double hydroxide was developed. In this case, two different ketene aminal phosphates were used as models to study the synthesis of α
