1196981-04-0Relevant articles and documents
Rhodium-Catalyzed Regioselective C7-Functionalization of N-Pivaloylindoles
Xu, Lanting,Zhang, Chao,He, Yupeng,Tan, Lushi,Ma, Dawei
, p. 321 - 325 (2016)
An efficient rhodium-catalyzed method for direct C-H functionalization at the C7 position of a wide range of indoles has been developed. Good to excellent yields of alkenylation products were observed with acrylates, styrenes, and vinyl phenyl sulfones, whereas the saturated alkylation products were obtained in good yield with α,β-unsaturated ketones. Both the N-pivaloyl directing group and the rhodium catalyst proved to be crucial for high regioselectivity and conversion.
Acyl-Directed ortho-Borylation of Anilines and C7 Borylation of Indoles using just BBr3
Iqbal, Saqib A.,Cid, Jessica,Procter, Richard J.,Uzelac, Marina,Yuan, Kang,Ingleson, Michael J.
supporting information, p. 15381 - 15385 (2019/10/22)
Indoles are privileged heterocycles found in many biologically active pharmaceuticals and natural products. However, the selective functionalization of the benzenoid moiety in indoles in preference to the more reactive pyrrolic unit is a significant challenge. Herein we report that N-acyl directing groups enable the C7-selective C?H borylation of indoles using just BBr3. This transformation shows some functional-group tolerance and notably proceeds with C6 substituted indoles. The directing group can be readily removed in situ and the products isolated as the pinacol boronate esters. Acyl-directed electrophilic borylation can be extended to carbazoles and anilines with excellent ortho selectivity. 4-amino-indoles are amenable to this process, with acyl group installation and directed electrophilic C?H borylation enabling selective formation of C5-BPin-indoles.
A Direct Access to 7-Aminoindoles via Iridium-Catalyzed Mild C-H Amidation of N-Pivaloylindoles with Organic Azides
Kim, Youyoung,Park, Juhyeon,Chang, Sukbok
supporting information, p. 1892 - 1895 (2016/05/19)
Ir(III)-catalyzed regioselective direct C-7 amidation of indoles in reaction with organic azides has been developed. While its efficiency was varied by the choice of N-directing groups, N-pivaloylindoles were most effective in undergoing the desired amidation at room temperature over a broad range of substrates. The reaction was scalable, and deprotection of the chelation group was also facile.
A systematic study of two complementary protocols allowing the general, mild and efficient deprotection of N-pivaloylindoles
Ruiz, Míriam,Sánchez, J. Domingo,López-Alvarado, Pilar,Menéndez, J. Carlos
experimental part, p. 705 - 710 (2012/01/06)
Two mild and general protocols for the high-yielding deprotection of indoles and related fused heterocyclic systems are described, involving either hydride transfer from LDA or hydrolysis by the DBU-water system. Both methods were shown to tolerate a wide variety of substituents and functional groups, but the hydrolytic one proved to be particularly general, being compatible with 2-alkyl substituents, aldehydes, ketones, carboxylic acids, halogens, ethers, amides and esters. Yields were normally excellent in both cases, but were usually slightly higher for the reductive method. Taken together, these two protocols provide a general solution to the problem of pivaloyindole deprotection.
Intermodular decarboxylative direct C-3 arylation of indoles with benzoic acids
Cornelia, Josep,Lu, Pengfel,Larrosa, Igor
supporting information; experimental part, p. 5506 - 5509 (2010/02/28)
"Chemical Equation Presented" A palladium catalyzed C-H activation of indoles and a silver catalyzed decarboxylative C-C activation of ortho substituted benzoic acids are synergistically combined to synthesize indoles arylated exclusively In the C-3 posit
