Highly efficient synthesis of aryl and heteroaryl trifluoromethyl ketones via o-iodobenzoic acid (IBX)

H Cheng, Y Pei, F Leng, J Li, A Liang, D Zou, Y Wu…

Index: Cheng, Huicheng; Pei, Yu; Leng, Faqiang; Li, Jingya; Liang, Apeng; Zou, Dapeng; Wu, Yangjie; Wu, Yusheng Tetrahedron Letters, 2013 , vol. 54, # 33 p. 4483 - 4486

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Citation Number: 11

Abstract

Abstract A two-step process for the synthesis of aryl and heteroaryl trifluoromethyl ketones from the corresponding aldehydes is described. Trifluoromethyl alcohols were prepared from aryl and heteroaryl aldehydes in excellent yields using catalytic amount of K 2 CO 3. The trifluoromethyl alcohols were then oxidized conveniently and efficiently by o- iodoxybenzoic acid (IBX) under mild conditions to get the desired functionalized aryl and ...

 Related Synthetic Route
(Trifluoromethyl)trimethylsilane Structure

81290-20-2

(Trifluoromethy...

4-Cyanobenzaldehyde Structure

105-07-7

4-Cyanobenzaldehyde

~99%

Benzonitrile, 4-(2,2,2-trifluoro-1-hydroxyethyl)- (9CI) Structure

107018-37-1

Benzonitrile, 4...

2,2,2-trifluoro-1-(naphthalen-1-yl)ethanol Structure

17556-44-4

2,2,2-trifluoro...

~99%

1-NAPHTHYL TRIFLUOROMETHYL KETONE Structure

6500-37-4

1-NAPHTHYL TRIF...

naphthal Structure

66-77-3

naphthal

~%

1-NAPHTHYL TRIFLUOROMETHYL KETONE Structure

6500-37-4

1-NAPHTHYL TRIF...

3-Nitrobenzaldehyde Structure

99-61-6

3-Nitrobenzaldehyde

(Trifluoromethyl)trimethylsilane Structure

81290-20-2

(Trifluoromethy...

~96%

2,2,2-TRIFLUORO-1-(3-NITROPHENYL)-ETHANOL Structure

453-77-0

2,2,2-TRIFLUORO...

1-phenyl-2,2,2-trifluoroethanol Structure

340-04-5

1-phenyl-2,2,2-...

~92%

2,2,2-Trifluoroacetophenone Structure

434-45-7

2,2,2-Trifluoro...

Benzaldehyde Structure

100-52-7

Benzaldehyde

~%

2,2,2-Trifluoroacetophenone Structure

434-45-7

2,2,2-Trifluoro...

(Trifluoromethyl)trimethylsilane Structure

81290-20-2

(Trifluoromethy...

4-Bromobenzaldehyde Structure

1122-91-4

4-Bromobenzaldehyde

~96%

(R)-1-(4-BROMOPHENYL)-2,2,2-TRIFLUOROETHANOL Structure

80418-12-8

(R)-1-(4-BROMOP...

(Trifluoromethyl)trimethylsilane Structure

81290-20-2

(Trifluoromethy...

Benzaldehyde Structure

100-52-7

Benzaldehyde

~96%

1-phenyl-2,2,2-trifluoroethanol Structure

340-04-5

1-phenyl-2,2,2-...

1-(5-bromopyridin-3-yl)-2,2,2-trifluoroethanol Structure

1204234-60-5

1-(5-bromopyrid...

~96%

1-(5-Bromo-3-pyridinyl)-2,2,2-trifluoroethanone Structure

886364-44-9

1-(5-Bromo-3-py...

6-Bromonicotinaldehyde Structure

113118-81-3

6-Bromonicotina...

~%

1-(5-Bromo-3-pyridinyl)-2,2,2-trifluoroethanone Structure

886364-44-9

1-(5-Bromo-3-py...

1-(4-chloropyridin-2-yl)-2,2,2-trifluoroethanol Structure

1346809-57-1

1-(4-chloropyri...

~95%

1-(4-chloropyridin-2-yl)-2,2,2-trifluoroethanone Structure

1356086-78-6

1-(4-chloropyri...

4-Chloropicolinaldehyde Structure

63071-13-6

4-Chloropicolin...

~%

1-(4-chloropyridin-2-yl)-2,2,2-trifluoroethanone Structure

1356086-78-6

1-(4-chloropyri...

1,4-Benzodioxane-6-aldehyde Structure

29668-44-8

1,4-Benzodioxan...

(Trifluoromethyl)trimethylsilane Structure

81290-20-2

(Trifluoromethy...

~97%

1-(2,3-Dihydro-1,4-benzodioxin-6-yl)-2,2,2-trifluoroethanol Structure

923170-94-9

1-(2,3-Dihydro-...

p-Tolualdehyde Structure

104-87-0

p-Tolualdehyde

(Trifluoromethyl)trimethylsilane Structure

81290-20-2

(Trifluoromethy...

~98%

2,2,2-trifluoro-1-p-tolylethanol Structure

446-65-1

2,2,2-trifluoro...

Benzenemethanol, 4-nitro-alpha-(trifluoromethyl)- (9CI) Structure

241127-76-4

Benzenemethanol...

~10%

2,2,2-TRIFLUORO-1-(4-IODO-PHENYL)-ETHANONE Structure

58808-61-0

2,2,2-TRIFLUORO...

2,2,2-TRIFLUORO-1-(3-METHOXYPHENYL) ETHANOL Structure

128816-77-3

2,2,2-TRIFLUORO...

~96%

2,2,2-Trifluoro-1-(3-methoxyphenyl)ethanone Structure

30724-22-2

2,2,2-Trifluoro...

1-(6-bromopyridin-3-yl)-2,2,2-trifluoroethanol Structure

1188477-81-7

1-(6-bromopyrid...

~97%

1-(6-broMopyridin-3-yl)-2,2,2-trifluoroethanone Structure

886364-47-2

1-(6-broMopyrid...

6-Bromonicotinaldehyde Structure

149806-06-4

6-Bromonicotina...

~%

1-(6-broMopyridin-3-yl)-2,2,2-trifluoroethanone Structure

886364-47-2

1-(6-broMopyrid...

3-Bromobenzaldehyde Structure

3132-99-8

3-Bromobenzaldehyde

(Trifluoromethyl)trimethylsilane Structure

81290-20-2

(Trifluoromethy...

~87%

1-(3-Bromophenyl)-2,2,2-trifluoroethanol Structure

446-63-9

1-(3-Bromopheny...

1-(2,3-Dihydro-1,4-benzodioxin-6-yl)-2,2,2-trifluoroethanol Structure

923170-94-9

1-(2,3-Dihydro-...

~10%

1-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-2,2,2-trifluoroethanone Structure

122243-34-9

1-(2,3-dihydrob...

1,4-Benzodioxane-6-aldehyde Structure

29668-44-8

1,4-Benzodioxan...

~%

1-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-2,2,2-trifluoroethanone Structure

122243-34-9

1-(2,3-dihydrob...

(+/-)-2,2,2-trifluoro-1-(4-chlorophenyl)ethanol Structure

72487-06-0

(+/-)-2,2,2-tri...

~95%

4'-chloro-2,2,2-trifluoroacetophenone Structure

321-37-9

4'-chloro-2,2,2...

(Trifluoromethyl)trimethylsilane Structure

81290-20-2

(Trifluoromethy...

3-Chlorobenzaldehyde Structure

587-04-2

3-Chlorobenzaldehyde

~98%

1-(3-chlorophenyl)-2,2,2-trifluoroethanol Structure

81577-11-9

1-(3-chlorophen...

2,2,2-Trifluoro-1-(2-methoxyphenyl)ethanol Structure

26902-84-1

2,2,2-Trifluoro...

~98%

2,2,2-Trifluoro-1-(2-methoxyphenyl)ethanone Structure

26944-43-4

2,2,2-Trifluoro...

(Trifluoromethyl)trimethylsilane Structure

81290-20-2

(Trifluoromethy...

4-hydroxybenzaldehyde Structure

123-08-0

4-hydroxybenzal...

~95%

4-(2,2,2-Trifluoro-1-hydroxyethyl)phenol Structure

246245-20-5

4-(2,2,2-Triflu...

3,4,5-Trimethoxybenzaldehyde Structure

86-81-7

3,4,5-Trimethox...

~%

2,2,2-Trifluoro-1-(3,4,5-trimethoxyphenyl)ethanone Structure

919530-43-1

2,2,2-Trifluoro...

(Trifluoromethyl)trimethylsilane Structure

81290-20-2

(Trifluoromethy...

2-Nitrobenzaldehyde Structure

552-89-6

2-Nitrobenzaldehyde

~96%

Benzenemethanol, 2-nitro-alpha-(trifluoromethyl)- (9CI) Structure

700362-32-9

Benzenemethanol...

1-(3-chlorophenyl)-2,2,2-trifluoroethanol Structure

81577-11-9

1-(3-chlorophen...

~95%

1-(3-Chlorophenyl)-2,2,2-trifluoroethanone Structure

321-31-3

1-(3-Chlorophen...

(Trifluoromethyl)trimethylsilane Structure

81290-20-2

(Trifluoromethy...

6-Bromonicotinaldehyde Structure

149806-06-4

6-Bromonicotina...

~94%

1-(6-bromopyridin-3-yl)-2,2,2-trifluoroethanol Structure

1188477-81-7

1-(6-bromopyrid...

1-(3-Bromophenyl)-2,2,2-trifluoroethanol Structure

446-63-9

1-(3-Bromopheny...

~10%

1-(3-BROMOPHENYL)-2,2,2-TRIFLUOROETHANONE Structure

655-26-5

1-(3-BROMOPHENY...

(Trifluoromethyl)trimethylsilane Structure

81290-20-2

(Trifluoromethy...

o-Anisaldehyde Structure

135-02-4

o-Anisaldehyde

~96%

2,2,2-Trifluoro-1-(2-methoxyphenyl)ethanol Structure

26902-84-1

2,2,2-Trifluoro...

(Trifluoromethyl)trimethylsilane Structure

81290-20-2

(Trifluoromethy...

2,4-Dichlorobenzaldehyde Structure

874-42-0

2,4-Dichloroben...

~99%

1-(2,4-dichlorophenyl)-2,2,2-trifluoroethanol Structure

1194760-60-5

1-(2,4-dichloro...

2,2,2-trifluoro-1-(4-methoxyphenyl)ethanol Structure

17556-42-2

2,2,2-trifluoro...

~99%

Ethanone,2,2,2-trifluoro-1-(4-methoxyphenyl)- Structure

711-38-6

Ethanone,2,2,2-...

2,2,2-TRIFLUORO-1-(3-NITROPHENYL)-ETHANOL Structure

453-77-0

2,2,2-TRIFLUORO...

~96%

2,2,2-Trifluoro-3'-nitroacetophenone Structure

657-15-8

2,2,2-Trifluoro...

5-Bromo-2-pyridinecarbaldehyde Structure

31181-90-5

5-Bromo-2-pyrid...

~%

1-(5-Bromo-2-pyridinyl)-2,2,2-trifluoroethanone Structure

886364-50-7

1-(5-Bromo-2-py...

Benzonitrile, 4-(2,2,2-trifluoro-1-hydroxyethyl)- (9CI) Structure

107018-37-1

Benzonitrile, 4...

~97%

4-(2,2,2-trifluoroacetyl)benzonitrile Structure

23516-85-0

4-(2,2,2-triflu...

naphthal Structure

66-77-3

naphthal

(Trifluoromethyl)trimethylsilane Structure

81290-20-2

(Trifluoromethy...

~93%

2,2,2-trifluoro-1-(naphthalen-1-yl)ethanol Structure

17556-44-4

2,2,2-trifluoro...

1-(2,4-dichlorophenyl)-2,2,2-trifluoroethanol Structure

1194760-60-5

1-(2,4-dichloro...

~99%

1-(2,4-Dichlorophenyl)-2,2,2-trifluoroethanone Structure

92736-81-7

1-(2,4-Dichloro...


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