210880-59-4Relevant academic research and scientific papers
Synthesis of 3-((trifluoromethyl)thio)indoles via trifluoromethylthiolation of 2-alkynyl azidoarenes with AgSCF3
Betterley, Nolan M.,Kuhakarn, Chutima,Leowanawat, Pawaret,Phetcharawetch, Jongkonporn,Reutrakul, Vichai,Soorukram, Darunee
supporting information, (2021/09/10)
Direct and effective trifluoromethylthiolation of 2-alkynyl azidoarenes with silver(I) trifluoromethanethiolate (AgSCF3) has been developed for the construction of 3-((trifluoromethyl)thio)indoles. The trifluoromethylthiolation protocol is compatible with a broad substrate scope, providing a variety of 3-((trifluoromethyl)thio)indoles in moderate to good yields within one step, open-air, and short reaction time.
Cyclization of Alkyne-Azide with Isonitrile/CO via Self-Relay Rhodium Catalysis
Zhang, Zhen,Xiao, Fan,Huang, Baoliang,Hu, Jincheng,Fu, Bin,Zhang, Zhenhua
, p. 908 - 911 (2016/03/15)
A self-relay rhodium(I)-catalyzed cyclization of alkyne-azides with two σ-donor/π-acceptor ligands (isonitriles and CO) to form sequentially multiple-fused heterocycle systems via tandem nitrene transformation and aza-Pauson-Khand cyclization has been dev
Umpolung reactivity of indole through gold catalysis
Lu, Biao,Luo, Yingdong,Liu, Lianzhu,Ye, Longwu,Wang, Yanzhao,Zhang, Liming
supporting information; experimental part, p. 8358 - 8362 (2011/10/31)
Electrophilic indole? Indoles, which are typically nucleophilic, can be made electrophilic through gold catalysis. By using an ortho-azido group to deliver a nitrene intramolecularly, an arylalkyne is converted into a gold carbene intermediate containing an indole skeleton that is highly electrophilic at the 3-position. A range of functionalized indoles is readily accessed by utilizing this strategy.
A study of vinyl radical cyclization onto the azido group by addition of sulfanyl, stannyl, and silyl radicals to alkynyl azides
Montevecchi, Pier Carlo,Navacchia, Maria Luisa,Spagnolo, Piero
, p. 1219 - 1226 (2007/10/03)
Thermal radical reactions of azidoalkynes 2, 8, 14, and 21a-c with thiols 1a-c afford 2-sulfanylvinyl radicals by selective addition of sulfanyl radicals to the triple bond. 1-Phenylvinyl radicals 23 and 30a, as well as vinyl radical 30b, undergo fast 5-cyclization onto the aromatic azide function to give cyclized indoles. In contrast, both 1-phenyl (15, 17) and 1-alkyl (3a,b, 9) vinyl radicals fail to add to their aliphatic azido substituents and exclusively undergo cyclization onto the aromatic sulfanyl ring and H transfer from the thiol precursor. Azidoalkynes 14 and 21a react with Bu3SnH and TMSS under radical conditions to give instead the corresponding amines as a result of preferential attack of Bu3Sn · and (TMS)3Si · radicals on the azido group rather than on the triple bond. Evidence is provided that alkyl radical cyclizations onto azides are not feasible in the presence of thiol, in contrast with the reported utility of these cyclization reactions in the presence of Bu3SnH and TMSS.
