e.g. Filippa Pettersson or Cancer Res. 75(6) , 1102-12, (2015) or 10.1002/anie.201600521

(Trifluoroacetyl) benzotriazole: A Convenient Trifluoroacetylating Reagent

AR Katritzky, B Yang, D Semenzin

Index: Katritzky, Alan R.; Yang, Baozhen; Semenzin, Delphine Journal of Organic Chemistry, 1997 , vol. 62, # 3 p. 726 - 728

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Citation Number: 74

Abstract

Trifluoroacetylation is important for the protection or activation of functional groups in organic and bioorganic synthesis. 1 Conventional reagents for trifluoroacetylation all have drawbacks or limitations:(i) trifluoroacetic anhydride2 has a low boiling point (39.5 C), is moisture sensitive, and is also too reactive for some applications;(ii) S-ethyl trifluorothioacetate forms the bad smelling by product ethanethiol; 3 (iii) ethyl ...

(Trifluoroacetyl)benzotriazole Structure

(Trifluoroacety...

Benzyl alcohol Structure

~94%

1H-Benzotriazole Structure

1H-Benzotriazole

Benzyl trifluoroacetate Structure

Benzyl trifluor...

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tert-Butylamine Structure

tert-Butylamine

(Trifluoroacetyl)benzotriazole Structure

(Trifluoroacety...

~97%

1H-Benzotriazole Structure

1H-Benzotriazole

N-(1-Hydroxy-2,2,2-trifluoroethylidene)-tert-butylamine Structure

N-(1-Hydroxy-2,...

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pentanol Structure

(Trifluoroacetyl)benzotriazole Structure

(Trifluoroacety...

~52%

1H-Benzotriazole Structure

1H-Benzotriazole

Acetic acid, 2,2,2-trifluoro-, pentyl ester Structure

Acetic acid, 2,...

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Piperidine Structure

(Trifluoroacetyl)benzotriazole Structure

(Trifluoroacety...

~0%

1H-Benzotriazole Structure

1H-Benzotriazole

1-Trifluoroacetyl piperidine Structure

1-Trifluoroacet...

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N-Ethylaniline Structure

(Trifluoroacetyl)benzotriazole Structure

(Trifluoroacety...

~0%

1H-Benzotriazole Structure

1H-Benzotriazole

N-ethyl-2,2,2-trifluoro-N-phenylacetamide Structure

N-ethyl-2,2,2-t...

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2-METHYLBUTYLAMINE Structure

2-METHYLBUTYLAMINE

(Trifluoroacetyl)benzotriazole Structure

(Trifluoroacety...

~0%

1H-Benzotriazole Structure

1H-Benzotriazole

Acetamide, 2,2,2-trifluoro-N-(2-Methylbutyl) Structure

Acetamide, 2,2,...

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p-tolylmethanol Structure

p-tolylmethanol

(Trifluoroacetyl)benzotriazole Structure

(Trifluoroacety...

~0%

1H-Benzotriazole Structure

1H-Benzotriazole

4-methylbenzyl trifluoroacetate Structure

4-methylbenzyl ...

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(R)-(+)-1-Phenylethylamine Structure

(R)-(+)-1-Pheny...

(Trifluoroacetyl)benzotriazole Structure

(Trifluoroacety...

~0%

1H-Benzotriazole Structure

1H-Benzotriazole

2,2,2-Trifluoro-N-[(1S)-1-phenylethyl]acetamide Structure

2,2,2-Trifluoro...

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4-Chlorophenol Structure

(Trifluoroacetyl)benzotriazole Structure

(Trifluoroacety...

~0%

1H-Benzotriazole Structure

1H-Benzotriazole

4-Chlorophenol trifluoroacetate Structure

4-Chlorophenol ...

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4-Nitroaniline Structure

(Trifluoroacetyl)benzotriazole Structure

(Trifluoroacety...

~0%

1H-Benzotriazole Structure

1H-Benzotriazole

2,2,2-Trifluoro-4'-nitroacetanilide Structure

2,2,2-Trifluoro...

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tert-Butylamine Structure

tert-Butylamine

(Trifluoroacetyl)benzotriazole Structure

(Trifluoroacety...

~0%

1H-Benzotriazole Structure

1H-Benzotriazole

N-(1-Hydroxy-2,2,2-trifluoroethylidene)-tert-butylamine Structure

N-(1-Hydroxy-2,...

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Naphthalen-2-amine Structure

Naphthalen-2-amine

(Trifluoroacetyl)benzotriazole Structure

(Trifluoroacety...

~0%

1H-Benzotriazole Structure

1H-Benzotriazole

Acetamide,2,2,2-trifluoro-N-2-naphthalenyl Structure

Acetamide,2,2,2...

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1-Phenylethanamine Structure

1-Phenylethanamine

(Trifluoroacetyl)benzotriazole Structure

(Trifluoroacety...

~0%

1H-Benzotriazole Structure

1H-Benzotriazole

2,2,2-trifluoro-N-[(4-methylphenyl)methyl]acetamide Structure

2,2,2-trifluoro...

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(Trifluoroacetyl)benzotriazole Structure

(Trifluoroacety...

Benzyl alcohol Structure

~0%

1H-Benzotriazole Structure

1H-Benzotriazole

Benzyl trifluoroacetate Structure

Benzyl trifluor...

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(Trifluoroacetyl)benzotriazole Structure

(Trifluoroacety...

4-Aminodiphenylamine Structure

4-Aminodiphenylamine

~0%

1H-Benzotriazole Structure

1H-Benzotriazole

N-(4-anilinophenyl)-2,2,2-trifluoroacetamide Structure

N-(4-anilinophe...

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Neopentyl alcohol Structure

Neopentyl alcohol

(Trifluoroacetyl)benzotriazole Structure

(Trifluoroacety...

~0%

1H-Benzotriazole Structure

1H-Benzotriazole

Acetic acid, 2,2,2-trifluoro-, 2,2-dimethylpropyl ester Structure

Acetic acid, 2,...

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(Trifluoroacetyl)benzotriazole Structure

(Trifluoroacety...

Cyclohexanol Structure

~0%

1H-Benzotriazole Structure

1H-Benzotriazole

Trifluoroacetic acid cyclohexyl Structure

Trifluoroacetic...

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pentanol Structure

(Trifluoroacetyl)benzotriazole Structure

(Trifluoroacety...

~0%

1H-Benzotriazole Structure

1H-Benzotriazole

Acetic acid, 2,2,2-trifluoro-, pentyl ester Structure

Acetic acid, 2,...

Learn More

4-Nitrophenol Structure

(Trifluoroacetyl)benzotriazole Structure

(Trifluoroacety...

~0%

1H-Benzotriazole Structure

1H-Benzotriazole

4-Nitrophenyltrifluoracetat Structure

4-Nitrophenyltr...

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1-Phenylethanamine Structure

1-Phenylethanamine

(Trifluoroacetyl)benzotriazole Structure

(Trifluoroacety...

~%

1H-Benzotriazole Structure

1H-Benzotriazole

Acetamide, 2,2,2-trifluoro-N-(1-phenylethyl) Structure

Acetamide, 2,2,...

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1H-Benzotriazole Structure

1H-Benzotriazole

Trifluoroacetic anhydride Structure

Trifluoroacetic...

~99%

(Trifluoroacetyl)benzotriazole Structure

(Trifluoroacety...

Learn More

Naphthalen-2-amine Structure

Naphthalen-2-amine

(Trifluoroacetyl)benzotriazole Structure

(Trifluoroacety...

~93%

1H-Benzotriazole Structure

1H-Benzotriazole

Acetamide,2,2,2-trifluoro-N-2-naphthalenyl Structure

Acetamide,2,2,2...

Learn More

(Trifluoroacetyl)benzotriazole Structure

(Trifluoroacety...

Cyclohexanol Structure

~82%

1H-Benzotriazole Structure

1H-Benzotriazole

Trifluoroacetic acid cyclohexyl Structure

Trifluoroacetic...

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(Trifluoroacetyl)benzotriazole Structure

(Trifluoroacety...

4-Aminodiphenylamine Structure

4-Aminodiphenylamine

~93%

1H-Benzotriazole Structure

1H-Benzotriazole

N-(4-anilinophenyl)-2,2,2-trifluoroacetamide Structure

N-(4-anilinophe...

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1-Phenylethanamine Structure

1-Phenylethanamine

(Trifluoroacetyl)benzotriazole Structure

(Trifluoroacety...

~94%

1H-Benzotriazole Structure

1H-Benzotriazole

2,2,2-trifluoro-N-[(4-methylphenyl)methyl]acetamide Structure

2,2,2-trifluoro...

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N-Ethylaniline Structure

(Trifluoroacetyl)benzotriazole Structure

(Trifluoroacety...

~85%

1H-Benzotriazole Structure

1H-Benzotriazole

N-ethyl-2,2,2-trifluoro-N-phenylacetamide Structure

N-ethyl-2,2,2-t...

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4-Nitroaniline Structure

(Trifluoroacetyl)benzotriazole Structure

(Trifluoroacety...

~90%

1H-Benzotriazole Structure

1H-Benzotriazole

2,2,2-Trifluoro-4'-nitroacetanilide Structure

2,2,2-Trifluoro...

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(R)-(+)-1-Phenylethylamine Structure

(R)-(+)-1-Pheny...

(Trifluoroacetyl)benzotriazole Structure

(Trifluoroacety...

~99%

1H-Benzotriazole Structure

1H-Benzotriazole

2,2,2-Trifluoro-N-[(1S)-1-phenylethyl]acetamide Structure

2,2,2-Trifluoro...

Learn More

4-Chlorophenol Structure

(Trifluoroacetyl)benzotriazole Structure

(Trifluoroacety...

~91%

1H-Benzotriazole Structure

1H-Benzotriazole

4-Chlorophenol trifluoroacetate Structure

4-Chlorophenol ...

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Erbium (III) triflate as an extremely active acylation catal...

[Procopio, Antonio; Dalpozzo, Renato; De Nino, Antonio; Maiuolo, Loredana; Russo, Beatrice; Sindona, Giovanni Advanced Synthesis and Catalysis, 2004 , vol. 346, # 12 p. 1465 - 1470]

Reaction of trifluoroacetic acid with alcohols, phenols, eth...

[Hagen, Arnulf P.; Miller, Tammy S.; Bynum, Richard L.; Kapila Ved P. Journal of Organic Chemistry, 1982 , vol. 47, # 7 p. 1345 - 1347]

2-(Trifluoroacetyloxy) pyridine as a mild trifluoroacetylati...

[Keumi, Takashi; Shimada, Masakazu; Morita, Toshio; Kitajima, Hidehiko Bulletin of the Chemical Society of Japan, 1990 , vol. 63, # 8 p. 2252 - 2256]

Hydrocarbon oxidations with chromyl trifluoroacetate

[Suggs, J. William; Ytuarte, Larry Tetrahedron Letters, 1986 , vol. 27, # 4 p. 437 - 440]

Hydrocarbon oxidations with chromyl trifluoroacetate

[Suggs, J. William; Ytuarte, Larry Tetrahedron Letters, 1986 , vol. 27, # 4 p. 437 - 440]