107734-12-3Relevant academic research and scientific papers
One-Pot Synthesis of Substituted Benzo[b]furans and Indoles from Dichlorophenols/Dichloroanilines Using a Palladium-Dihydroxyterphenylphosphine Catalyst
Yamaguchi, Miyuki,Akiyama, Tomoyo,Sasou, Hirohisa,Katsumata, Haruka,Manabe, Kei
, p. 5450 - 5463 (2016/07/14)
Disubstituted benzo[b]furans were synthesized by ortho-selective Sonogashira coupling of dichlorophenols and terminal alkynes, followed by cyclization and Suzuki-Miyaura coupling in one pot, using a palladium-dihydroxyterphenylphosphine (Cy-DHTP) catalyst. The use of substoichiometric amounts of tetrabutylammonium chloride was effective in accelerating the Suzuki-Miyaura coupling. This protocol was also successfully applied to the one-pot synthesis of disubstituted indoles from dichloroaniline derivatives.
Silver(I)-mediated C-H amination of 2-alkenylanilines: Unique solvent-dependent migratory aptitude
Youn, So Won,Ko, Tae Yun,Jang, Min Jung,Jang, Su San
supporting information, p. 227 - 234 (2015/01/30)
A highly effective silver(I)-mediated C-H amination of 2-alkenylanilines has been developed to afford a diverse range of substituted indoles. High functional group tolerance, broad substrate scope, simple/fast/high-yielding reaction, and recovery/reuse of the inexpensive silver oxidant are noteworthy. Furthermore, an uncommon migratory process of β-monosubstituted 2-alkenylanilines with solvent-dependence was demonstrated.
Metal-free C-H amination for indole synthesis
Jang, Young Ho,Youn, So Won
supporting information, p. 3720 - 3723 (2014/08/05)
An effective metal-free C-H amination of N-Ts-2-alkenylanilines by using DDQ as an oxidant has been developed to afford a diverse range of substituted indoles. This protocol is operationally simple and robust, obviates the need of expensive transition-metal catalysts, and offers a broad substrate scope. A mechanism involving a radical cation generated by SET and a migratorial process via a phenonium ion intermediate is proposed.
Synthesis of 3-carboxylated indoles through a tandem process involving cyclization of 2-ethynylanilines followed by CO2 fixation in the absence of transition metal catalysts
Inamoto, Kiyofumi,Asano, Narumi,Nakamura, Yuka,Yonemoto, Misato,Kondo, Yoshinori
supporting information; experimental part, p. 2622 - 2625 (2012/07/14)
In this study, a facile synthesis of 3-carboxylated indoles involving a tandem-type cyclization of 2-ethynylanilines and subsequent CO2 fixation at the 3-position of the indole ring is realized. The reaction proceeds efficiently at 65 °C under
Palladium-free zinc-mediated hydroamination of alkynes: efficient synthesis of indoles from 2-akynylaniline derivatives
Okuma, Kentaro,Seto, Jun-ichi,Sakaguchi, Ken-ichi,Ozaki, Saori,Nagahora, Noriyoshi,Shioji, Kosei
supporting information; experimental part, p. 2943 - 2945 (2009/07/26)
Reaction of 2-phenylethynyl N-tosylanilide prepared by Pd-free procedure with ZnBr2 (3 equiv) in refluxing toluene gave N-tosyl-2-phenylindole in 93% yield. Treatment of 2-phenylethynylaniline with ZnBr2 (1 equiv) in refluxing toluene resulted in the formation of 2-phenylindole in 91% yield. Catalytic ZnBr2 (0.05 equiv) effectively reacted with 2-alkynylanilines to afford 2-substituted indoles in high yields. Thus, complete Pd-free zinc catalyzed hydroamination of 2-alkynylanilines was achieved.
