79655-96-2Relevant academic research and scientific papers
Enantioselective Rauhut–Currier Reaction with β-Substituted Acrylamides Catalyzed by N-Heterocyclic Carbenes
Pitchumani, Venkatachalam,Breugst, Martin,Lupton, David W.
supporting information, p. 9413 - 9418 (2021/12/09)
β-Substituted acrylamides have low electrophilicity and are yet to be exploited in the enantioselective Rauhut–Currier reaction. By exploiting electron-withdrawing protection of the amide and moderate nucleophilicity N-heterocyclic carbenes, such substrates have been converted to enantioenriched quinolones. The reaction proceeds with complete diastereoselectivity, good yield, and modest enantioselectivity. Derivatizations are reported, as are computational studies, supporting decreased amide bond character with electron-withdrawing protection of the nitrogen.
Design and application of intramolecular vinylogous Michael reaction for the construction of 2-alkenyl indoles
Harish, Battu,Yadav, Sanjay,Suresh, Surisetti
supporting information, p. 231 - 234 (2021/01/14)
A base-mediated transformation based on a designed intramolecular vinylogous Michael addition (intra-VMA) is presented to access 3-substituted 2-alkenyl indole derivatives. The reaction represents the first example of the intra-VMA for the construction of
Visible-Light-Induced Decarboxylative Cyclization of 2-Alkenylarylisocyanides with α-Oxocarboxylic Acids: Access to 2-Acylindoles
Zhang, Xiaofei,Zhu, Peiyuan,Zhang, Ruihong,Li, Xiang,Yao, Tuanli
, p. 9503 - 9513 (2020/09/03)
An efficient and practical protocol for visible-light-induced decarboxylative cyclization of 2-alkenylarylisocyanides with α-oxocarboxylic acids has been developed, which afforded a broad range of 2-acylindoles in moderate to good yields. The reaction proceeds through a cascade of acyl radical addition/cyclization reactions under irradiation of an Ir3+ photoredox catalyst without external oxidants and features simple operation, scalability, a broad substrate scope, and good functional group tolerance.
Synthesis of Highly Substituted 2-Arylindoles via Copper-Catalyzed Coupling of Isocyanides and Arylboronic Acids
Heckman, Laurel M.,He, Zhi,Jamison, Timothy F.
supporting information, p. 3263 - 3267 (2018/06/11)
Highly functionalized 2-arylindoles were synthesized from 2-alkenylarylisocyanides and arylboronic acids using a simple, inexpensive copper catalyst. The reaction exhibits excellent functional group tolerance for both the arylisocyanide and boronic acid coupling partners. To avoid the direct handling of the pungent arylisocyanide starting materials, continuous flow chemistry is further demonstrated to provide safe and effective access to 2-arylindoles through in situ dehydration and cyclization of easy-to-handle 2-alkenyl-N-formylanilines.
Recycled Pd/C-Catalyzed Heck Reaction of 2-Iodoanilines under Ligand-Free Conditions
Zhou, Xiao-Yu,Chen, Xia,Wang, Liang-Guang
supporting information, p. 5364 - 5370 (2017/12/14)
Recyclable Pd/C-catalyzed Heck reaction of 2-iodoanilines with acrylate has been developed. The reaction occurred readily in 1,4-dioxane using Pd/C (10 wt%) as catalyst under ligand-free conditions, and the cross-coupling products were obtained with medium to high yield. Gram-scale reactions and recycling of the catalyst were also demonstrated.
Coupling Radical Homoallylic Expansions with C-C Fragmentations for the Synthesis of Heteroaromatics: Quinolines from Reactions of o-Alkenylarylisonitriles with Aryl, Alkyl, and Perfluoroalkyl Radicals
Evoniuk, Christopher J.,Gomes, Gabriel Dos Passos,Ly, Michelle,White, Frankie D.,Alabugin, Igor V.
, p. 4265 - 4278 (2017/04/27)
Selective addition of radicals to isonitriles can be harnessed for initiating reaction cascades designed to overcome the stereoelectronic restrictions on homoallylic ring expansion in alkyne reactions and to develop a new general route for the preparation of N-heteroaromatics. This method utilizes alkenes as synthetic equivalents of alkynes by coupling homoallylic ring expansion to yield the formal "6-endo" products with aromatization via stereoelectronically assisted C-C bond scission. Computational analysis of the homoallyic expansion potential energy surface reveals that the indirect 5-exo/3-exo/retro-3-exo path is faster than the direct 6-endo-trig closure, revealing the general exo-preference for the cyclization processes.
Palladium catalyzed Heck reaction of 2-iodoanilines under ligand-free conditions in air
Chen, Xia,Zhou, Xiao-Yu,Wang, Liang-Guang
supporting information, p. 2096 - 2102 (2017/10/26)
Palladium catalyzed Heck reaction of 2-iodoanilines and acrylate has been developed. The palladium catalyzed Heck reaction of 2-iodoanilines can readily occur in CH3CN using Pd(OAc)2 (5.0 mol%) as catalyst, NEt3 as base un
3-Trifluoromethylated Coumarins and Carbostyrils by Radical Trifluoromethylation of ortho-Functionalized Cinnamic Esters
Chaabouni, Slim,Simonet, Florent,Fran?ois, Alison,Abid, Souhir,Galaup, Chantal,Chassaing, Stefan
supporting information, p. 271 - 277 (2017/01/24)
A method for the trifluoromethylation of ortho-hydroxycinnamic esters was developed to achieve the regioselective synthesis of 3-trifluoromethylated coumarins. The reaction was performed by using the Togni reagent as the CF3source under mild conditions and showed good functional- group tolerance. The scope of this copper-mediated method was further expanded to the synthesis of 3-trifluoromethylated carbostyrils starting from ortho-aminocinnamic derivatives. Interestingly, a sequential one-pot synthesis of 3-trifluoromethylated coumarins starting from salicylaldehydes was further developed. The mechanism of this cascade reaction was explored, and a radical pathway was found to be consistent with the obtained results.
Double C-H amination by consecutive SET oxidations
Evoniuk, Christopher J.,Hill, Sean P.,Hanson, Kenneth,Alabugin, Igor V.
supporting information, p. 7138 - 7141 (2016/06/09)
A new method for intramolecular C-H oxidative amination is based on a FeCl3-mediated oxidative reaction of anilines with activated sp3 C-H bonds. The amino group plays multiple roles in the reaction cascade: (1) as the activating group in single-electron-transfer (SET) oxidation process, (2) as a directing group in benzylic/allylic C-H activation at a remote position, and (3) internal nucleophile trapping reactive intermediates formed from the C-H activation steps. These multielectron oxidation reactions proceed with catalytic amounts of Fe(iii) and inexpensive reagents.
