727416-65-1Relevant academic research and scientific papers
Palladium-Catalyzed Oxidative Annulation of ortho-Alkenylanilines and Allenes: An Access to Benzo[b]azepines
Wu, Lisha,Meng, Yinfeng,Ferguson, Jamie,Wang, Lijie,Zeng, Fanlong
, p. 4121 - 4128 (2017)
Palladium-catalyzed oxidative annulation of ortho-alkenylanilines and allenes to constitute valuable, but synthetically challenging, benzo[b]azepines has been developed. The procedure, involving the cleavage of the terminal C(sp2)-H bond of the vinyl moiety and the participation of allenes as two-carbon cycloaddition partner, is attractive in terms of assembly efficiency and environmental friendliness. The transformation features mild reaction conditions and good functional group tolerance, resulting in a variety of benzo[b]azepines in good to excellent yields.
Electrocatalytic Dehydrogenative Cyclization of 2-Vinylanilides for the Synthesis of Indoles
Zheng, Yun-Tao,Song, Jinshuai,Xu, Hai-Chao
, p. 16001 - 16007 (2021/08/20)
Indole is prevalent in bioactive compounds and natural products. The development of efficient and sustainable methods to access this privileged structural scaffold has been a long-standing interest of synthetic chemists. Herein, we report an electrocataly
Palladium(II)/Lewis acid cocatalyzed oxidative annulation of 2-alkenylanilines and propargylic esters: An access to benzo[ b]azepines
Qiao, Hong,Zhang, Shengjun,Li, Kangkang,Cao, Zhengqiang,Zeng, Fanlong
, p. 10843 - 10851 (2019/09/12)
An attractive approach to valuable yet synthetically challenging benzo[b]azepines was established via palladium(II)/Lewis acid cocatalyzed oxidative [5 + 2] annulation of readily available 2-alkenylanilines and propargylic esters. The protocol features mild reaction conditions and good functional group tolerance, constituting an array of benzo[b]azepines in yields of 30-75%.
Palladium-Catalyzed Sequential Vinylic C-H Arylation/Amination of 2-Vinylanilines with Aryl boronic Acids: Access to 2-Arylindoles
Yu, Ruixia,Li, Dejun,Zeng, Fanlong
, p. 323 - 329 (2018/02/19)
A palladium-catalyzed selective and successive vinylic C-H arylation/amination of 2-vinylanilines with arylboronic acids to generate indoles has been developed. This procedure represents a straightforward and practical approach to valuable multifunctionalized indoles.
Iodine(III) Reagent-Mediated Intramolecular Amination of 2-Alkenylanilines to Prepare Indoles
Zhao, Chun-Yang,Li, Kun,Pang, Yu,Li, Jia-Qing,Liang, Cui,Su, Gui-Fa,Mo, Dong-Liang
supporting information, p. 1919 - 1925 (2018/03/28)
A variety of 3-substituted and 2,3-disubstituted indoles were synthesized efficiently in good yields through the intramolecular amination of 2-alkenylanilines promoted by readily available iodine(III) reagents in a short reaction time. Mechanistic studies showed that the reaction pathway went through a nitrenium ion and that 3-acetoxy indoline was the key intermediate in the indole formation. The indole product was easily prepared on a gram scale and amination also proceeded smoothly using catalytic 3,5-dimethylphenyl iodine in the presence of mCPBA. Furthermore, the indolo[3,2-a]carbazole scaffold was prepared in good yield in six steps from commercial ortho-iodoaniline. (Figure presented.).
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.
The cooperative FeCl3/DDQ system for the regioselective synthesis of 3-arylindoles from β-monosubstituted 2-alkenylanilines
Jang, Su San,Youn, So Won
, p. 2200 - 2204 (2016/03/01)
A highly regioselective synthesis of 3-arylindoles by using the cooperative FeCl3/DDQ system has been developed. This new protocol represents an attractive route for the synthesis of 3-arylindoles from readily accessible non-indole precursors, β-aryl-substituted 2-styrylanilines, using an inexpensive catalyst and oxidant. Noteworthy is the unique synergetic and synergistic effect of FeCl3 and DDQ on the 1,2-aryl migratory process.
Unusual 1,2-aryl migration in Pd(II)-catalyzed aza-Wacker-type cyclization of 2-alkenylanilines
Youn, So Won,Lee, So Ra
supporting information, p. 4652 - 4656 (2015/04/27)
Inspired by the Hegedus aza-Wacker indole synthesis, we were intrigued with the fate of the aminopalladation intermediate if syn β-hydrogen is made inaccessible or unavailable. In contrast to our previously reported β-carbon elimination, cyclization of a
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.
Direct C-H amination for indole synthesis from N-Ts-2-Styrylaniline derivatives catalyzed by copper salt
Chen, Di,Mo, Han-Jie,Chen, Ding-Ben,Yang, Jian-Guo
, p. 969 - 972 (2015/08/24)
Abstract A direct C-H amination reaction of N-Ts-2-Styrylaniline derivatives to realize the synthesis of indole derivatives was developed in the presence of copper salt. A variety of N-Ts-2-Styrylaniline derivatives were transformed into the corresponding
