114650-12-3Relevant academic research and scientific papers
Indolylzinc iodides by oxidative addition of active zinc to iodoindoles
Sakamoto, Takao,Kondo, Yoshinori,Takazawa, Nobuo,Yamanaka, Hiroshi
, p. 5955 - 5956 (1993)
Indolylzinc derivatives were prepared by the oxidative addition of active zinc to iodoindoles, which coupled with aromatic halides in the presence of palladium catalyst to give arylated indoles.
Halogen-magnesium exchange reaction of iodoindole derivatives
Kondo, Yoshinori,Yoshida, Akihiro,Sato, Shuichiroh,Sakamoto, Takao
, p. 105 - 108 (1996)
Halogen-magnesium exchange reaction of iodoindoles with ethylmagnesium bromide in THF undergoes smoothly to give indolylmagnesium bromides which react with various electrophiles.
Palladium-Catalyzed Regioselective Synthesis of 3-Arylindoles from N-Ts-Anilines and Styrenes
Youn, So Won,Ko, Tae Yun,Jang, Young Ho
, p. 6636 - 6640 (2017/05/29)
A Pd-catalyzed intermolecular oxidative annulation between N-Ts-anilines and styrenes was developed. This method offers a straightforward and robust approach to a wide range of 3-arylindoles using readily available starting materials with good functional-group tolerance and high regioselectivity and efficiency. Further elaboration of the products obtained from this process provided access to highly functionalized and structurally diverse indoles, for example, 3-(indol-3-yl)carbazoles, 1,9-dihydropyrrolo-[2,3-b]carbazoles, and 3′-aryl-3,5′-biindoles.
A concise approach to indoles via oxidative C-H amination of 2-alkenylanilines using dioxygen as the sole oxidant
Ma, Ai-Lun,Li, Yin-Long,Li, Jian,Deng, Jun
, p. 35764 - 35770 (2016/05/19)
A novel synthetic method to prepare indole derivatives from N-Ts-2-alkenylanilines has been achieved. This reaction is through an oxidative intramolecular C-H amination by using molecular oxygen as the sole oxidant. This protocol is operationally simple a
In-Depth Assessment of the Palladium-Catalyzed Fluorination of Five-Membered Heteroaryl Bromides
Milner, Phillip J.,Yang, Yang,Buchwald, Stephen L.
supporting information, p. 4775 - 4780 (2015/10/28)
A thorough investigation of the challenging Pd-catalyzed fluorination of five-membered heteroaryl bromides is presented. Crystallographic studies and density functional theory (DFT) calculations suggest that the challenging step of this transformation is
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
, 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.
Regiocontrolled aerobic oxidative coupling of indoles and benzene using Pd catalysts with 4,5-diazafluorene ligands
Campbell, Alison N.,Meyer, Eric B.,Stahl, Shannon S.
supporting information; experimental part, p. 10257 - 10259 (2011/10/19)
Palladium-catalyzed aerobic oxidative cross-couplings of indoles and benzene have been achieved by using 4,5-diazafluorene derivatives as ancillary ligands. Proper choice of the neutral and anionic ligands enables control over the reaction regioselectivit
The synthesis of 2- and 3-aryl indoles and 1,3,4,5-tetrahydropyrano[4,3-b]indoles and their antibacterial and antifungal activity
Leboho, Tlabo C.,Michael, Joseph P.,van Otterlo, Willem A.L.,van Vuuren, Sandy F.,de Koning, Charles B.
scheme or table, p. 4948 - 4951 (2009/12/24)
A series of 2- and 3-aryl substituted indoles and two 1,3,4,5-tetrahydropyrano[4,3-b]indoles were synthesized from indole and 5-methoxyindole. The 2-aryl indoles were synthesized from the 1-(phenylsulfonyl)indole derivatives using magnesiation followed by iodination. The 2-iodinated compounds were then subjected to Suzuki-Miyaura reactions. In addition, the 3-aryl indoles were made from the corresponding 3-bromoindoles using Suzuki-Miyaura reactions. The 1,3,4,5-tetrahydropyrano[4,3-b]indoles were also synthesized from 1-(phenylsulfonyl)indole by magnesiation followed by treatment with allylbromide. The product was then converted into [2-allyl-1-(phenylsulfonyl)-1H-indol-3-yl]methanol which upon exposure to Hg(OAc)2 and NaBH4 afforded tetrahydropyrano[4,3-b]indoles. A number of the 2- and 3-aryl indoles displayed noteworthy antimicrobial activity, with compound 13a displaying the most significant activity (3.9 μg/mL) against the Gram-positive micro-organism Bacillus cereus.
Synthesis of new fused and substituted benzo and pyrido carbazoles via C-2 (het)arylindoles
Bourderioux, Aurélie,Kassis, Paméla,Mérour, Jean-Yves,Routier, Sylvain
experimental part, p. 11012 - 11019 (2009/04/11)
In the course of a program aimed at designing new antitumor agents, we were interested in the synthesis of new substituted benzo and pyrido carbazoles. The synthesis was performed through an efficient four-step sequence from a 2-trimethylstannylindole derivative and via C-2 (het)arylindoles. The synthetic sequence was developed using two palladium mediated reactions including, at the end of the synthesis, a direct (het)arylannulation, which led to the desired heterocycles.
