An alternative route for synthesis of o-trifluoroacetylanilines as useful fluorine-containing intermediates

Indium-Catalyzed Annulation of o-Acylanilines with Alkoxyheteroarenes: Synthesis of Heteroaryl[b]quinolines and Subsequent Transformation to Cryptolepine Derivatives

“…92–94 °C). Compound 2g has already appeared in the literature [ 87 ], and its spectral and analytical data are in good agreement with those reported. Accordingly, only the 1 H-NMR data are provided here.…”

“…MeOH was stored over molecular sieves 3Å (MS 3Å) under argon. The following indium salts and substrates were synthesized according to the respective literature methods: In(NTf 2 ) 3 [ 83 , 84 ], In(ONf) 3 [ 56 , 85 ], 1-(2-aminophenyl)-2-methyl-1-propanone ( 2e ) [ 86 ], 1-(2-aminophenyl)-2,2,2-trifluoroethanone ( 2f ) [ 87 ], (2-aminophenyl)(4-methoxyphenyl)methanone ( 2j ) [ 88 ], (2-aminophenyl)(2-methylphenyl)methanone ( 2l ) [ 88 ], 3-methoxybenzo[ b ]thiophene ( 3a ) [ 89 ], 2-methoxybenzo[ b ]thiophene ( 3b ) [ 54 ], 2-methoxy-5-methylthiophene ( 3d ) [ 54 ], 2-methoxybenzo[ b ]furan ( 3f ) [ 54 ], 2-methoxy-5-phenylfuran ( 3g ) [ 54 ], 2-methoxy-1-phenyl-1 H -pyrrole ( 3h ) [ 54 ]. Unless otherwise noted, other substrates and reagents were commercially available, and used as received without further purification.…”

Copper‐Mediated Trifluoroacetylation of Arenediazonium Salts with Ethyl Trifluoropyruvate

“…[10] Consequently,s ubstantial at-tention hasb een paid to develop efficient methods for TMFKs synthesis and, in the recent past, numerous new synthetic protocolsh ave been reported (Scheme 1). [11] They rely on traditionalr eactionsi ncluding Friedel-Crafts acylation, [12] Grignard reaction, [13] ortho-lithiation, [14] oxidation of trifluoromethyl alcohols, [15] nucleophilic trifluoromethylation of esters or amide with trifluoromethyl agent, [16] Suzuki-Miyaura cross-coupling reaction, [17] Wittig reaction with trifluoroacetamides, [18] and other methods. [19] Although these proceduresp rovide av iable route for the synthesis of TFMKs, necessary use of toxic andexpensive reagents, multistep reactions equences, the requirement of severe experimental conditions, and low yields or lack of regioselectivity in the formation of the trifluoroacetyl group limits their potentiala pplication.T hus,t he development of am ild and operationally simple strategy fort he construction of trifluoromethyl aryl ketones from readily available starting materials is highly desirable.…”

En Route to 2-(Cyclobuten-1-yl)-3-(trifluoromethyl)-1H-indole

“…The Journal of Organic Chemistry Hz, 3H). 13 C NMR (126 MHz, CDCl 3 ): δ 160.0, 132.7, 128.6, 127.1 (q, J = 3.7 Hz), 126.8, 125.7 (q, J = 1.5 Hz), 123.3 (q, J = 268.2 Hz), 121.2 (q, J = 3.5 Hz), 113.2, 109.4 (q, J = 37.9 Hz), 62.4, 13.9 (17). To an ice-cold stirred solution of 1-(2-amino-5-chlorophenyl)-2,2,2-trifluoroethan-1-one (12, 357 mg, 1.60 mmol), pyridine (139 mg, 142 μL, 1.75 mmol), and CH 2 Cl 2 (12 mL) was slowly added cyclobutanecarbonyl chloride (15c, 189 mg, 184 μL, 1.60 mmol).…”

“…A low-valent titanium reductive dimerization of aldehydes and ketones to alkenes, known as the McMurry reaction, has been developed by Fürstner and co-workers into a convenient and flexible method for the construction of indole scaffold starting form N ,2-diacetylanilines. To assess this idea, the required starting 4-chloro-2-trifluoroacetylaniline ( 12 ) was provided from the commercial 4-chloroaniline by a known procedure Scheme ).…”