116757-91-6Relevant academic research and scientific papers
α-Trifluoromethyl-(indol-3-yl)methanols as trifluoromethylated C3 1,3-dipoles: [3+2] cycloaddition for the synthesis of 1-(trifluoromethyl)-cyclopenta[b]indole alkaloids
Dong, Jinhuan,Pan, Ling,Xu, Xianxiu,Liu, Qun
, p. 14797 - 14800 (2014)
The first formal [3+2] cycloaddition using α-trifluoromethyl-(indol-3-yl)methanols as the trifluoromethylated C3 1,3-dipoles for the construction of the five-membered carbocycle of 1-trifluoromethylated cyclopenta[b]indole alkaloids is describe
Friedel-Crafts Fluoroacetylation of Indoles with Fluorinated Acetic Acids for the Synthesis of Fluoromethyl Indol-3-yl Ketones under Catalyst- and Additive-Free Conditions
Yao, Shun-Jiang,Ren, Zhi-Hui,Wang, Yao-Yu,Guan, Zheng-Hui
, p. 4226 - 4234 (2016)
A simple and efficient protocol for the fluoroacetylation of indoles is reported. The reaction uses fluorinated acetic acids as the fluoroacetylation reagents to synthesize diverse fluoromethyl indol-3-yl ketones in good yields under catalyst- and additive-free conditions. In addition, the only byproduct is water in this transformation. The synthetic utility of this reaction was also demonstrated by the concise synthesis of α-(trifluoromethyl)(indol-3-yl)methanol and indole-3-carboxylic acid.
Copper-Catalyzed Functionalization of Aza-Aromatic Rings with Fluoroalcohols via Direct C(sp2)-H/C(sp3)-H Coupling Reactions
Chen, Jie,Jiang, Yaojia,Li, Meng,Sun, Wangbin,Zhang, Jinli
, p. 3033 - 3038 (2020)
An efficient copper-catalyzed direct C(sp2)-H/C(sp3)-H coupling reaction of aza-aromatic rings with fluoroalcohols is developed. A variety of useful building blocks including hydroxyfluoroalkylated aniline, pyrrole, and indole derivatives bearing a quaternary carbon center could be constructed with high regioselectivity and good to excellent yields under very mild reaction conditions. The reaction is believed to undergo a fluoroalcohol oxidation and to follow an electronic addition reaction pathway.
TEMPO-Mediated Cross-Dehydrogenative Coupling of Indoles and Imidazo[1,2- a]pyridines with Fluorinated Alcohols
Nipate, Dhananjay S.,Jaspal, Sonam,Shinde, Vikki N.,Rangan, Krishnan,Kumar, Anil
supporting information, p. 1373 - 1377 (2021/02/20)
A simple and highly efficient metal-free method has been developed for hydroxyfluoroalkylation of indoles and imidazo[1,2-a]pyridines via TEMPO-mediated C(sp3)-H and C(sp2)-H bond cross-dehydrogenative coupling of fluorinated alcohols and indoles. The protocol showed broad substrate scope, afforded good yields of hydroxyfluoroalkylated products, and was amenable for scale-up. Mechanistic investigation indicated involvement of the radical pathway.
High-throughput screening of bioactive compounds via new catalytic reaction in the pooled mixture
Satoh, Ayano,Nishina, Yuta
, (2019/08/20)
To increase the chances of finding new candidate molecules with medicinal properties, while expending less resource and effort, the present study used pooled substrates as starting materials. A bisindole compound that showed inhibitory activity was then isolated from the mixture, and the activity was improved by optimizing the substituents on the indole skeleton.
A Free-Radical-Promoted Site-Specific Cross-Dehydrogenative-Coupling of N-Heterocycles with Fluorinated Alcohols
Xu, Zhengbao,Hang, Zhaojia,Chai, Li,Liu, Zhong-Quan
supporting information, p. 4662 - 4665 (2016/09/28)
A C-C formation of an electron-rich N-heterocycle with fluorinated alcohol is developed. Through this radical-triggered cross-dehydrogenative coupling strategy, a wide range of useful building blocks such as C3 hydroxyfluoroalkylated indoles and pyrroles can be site-specifically synthesized. Mechanistic studies indicate a single-electron-transfer initiated radical cycle would be involved.
Mixed-Metal MIL-100(Sc,M) (M=Al, Cr, Fe) for Lewis acid catalysis and tandem C-C Bond formation and alcohol oxidation
Mitchell, Laura,Williamson, Patrick,Ehrlichov, Barbora,Anderson, Amanda E.,Seymour, Valerie R.,Ashbrook, Sharon E.,Acerbi, Nadia,Daniels, Luke M.,Walton, Richard I.,Clarke, Matthew L.,Wright, Paul A.
supporting information, p. 17185 - 17197 (2015/02/19)
The trivalent metal cations Al3+, Cr3+, and Fe3+ were each introduced, together with Sc3+, into MIL- 100(Sc,M) solid solutions (M=Al, Cr, Fe) by direct synthesis. The substitution has been confirmed by powder X-
Enantioselective Friedel-Crafts reaction of indoles with trifluoroacetaldehyde catalyzed by Cinchona alkaloids
Borkin, Dmitry A.,Landge, Shainaz M.,Toeroek, Bela
experimental part, p. 612 - 616 (2011/12/15)
The first direct asymmetric synthetic preparation of trifluoro-1-(indol-3- yl)ethanols (TFIEs) is described by an enantioselective organocatalytic method from indoles and inexpensive trifluoroacetaldehyde methyl hemiacetal. The reaction is catalyzed by hydroquinine to produce TFIEs in an almost quantitative yield and with enantioselectivities up to 75% at room temperature. The enantioselectivity is strongly dependent on the concentration of substrates and catalyst due to the competitive noncatalyzed reaction. Copyright
Synthesis of indole-3-carboxamides via a haloform cleavage reaction of 3-trifluoroacetylindole with lithium dialkylamides
Hassinger, Heidi L.,Soll, Richard M.,Gribble, Gordon W.
, p. 3095 - 3098 (2007/10/03)
Reaction of 3-trifluoroacetylindole (4) with lithium dialkylamides affords the corresponding indole-3-carboxamides (5) in good to excellent yields.
THERMAL CONDENSATION OF INDOLES WITH TRIFLUOROACETALDEHYDE
Maki, Yasuo,Kimoto, Hiroshi,Fujii, Shozo,Senga, Munehiro,Cohen, Louis A.
, p. 47 - 60 (2007/10/02)
The title condensations provide the corresponding (1'-hydroxy-2',2',2'-trifluoroethyl)indoles.Indole itself, 1-methylindole and 2-methylindole gave 3-adducts in yields of 77percent, 49percent and 84percent, respectively. 3-Substituted indoles (3-methylindole, ethyl indole-3-acetate and indole-3-ethyl acetate) afforded 2-adducts in yields of 69percent, 21percent and 23percent, respectively.The indole adduct eliminates water at 137 deg C to form a transient 3-(trifluoromethylmethylene)indolenine, which reacts rapidly with nucleophiles including indole.
