Organic letters

Direct Intermolecular Aniline Ortho-Arylation via Benzyne Intermediates

T Truong, O Daugulis

Index: Truong, Thanh; Daugulis, Olafs Organic Letters, 2012 , vol. 14, # 23 p. 5964 - 5967

Full Text: HTML

Citation Number: 11

Abstract

A method for direct, transition-metal-free ortho-arylation of anilines by aryl chlorides, bromides, fluorides, and triflates has been developed. This methodology provides the most direct approach to 2-arylanilines since no protecting or directing groups on nitrogen are required. The arylation is functional-group tolerant, with alkene, ether, trifluoromethyl, dimethylamino, carbonyl, chloro, and cyano functionalities tolerated. Phenylation of ...

 Related Synthetic Route
phenyl trifluoromethanesulfonate Structure

17763-67-6

phenyl trifluor...

4-Chloroaniline Structure

106-47-8

4-Chloroaniline

~60%

4-chloro-2-phenyl-aniline Structure

73006-78-7

4-chloro-2-phen...

2-Chloroanisole Structure

766-51-8

2-Chloroanisole

Naphthalen-2-amine Structure

91-59-8

Naphthalen-2-amine

~9%

1-(3-methoxy)-2-naphthylamine Structure

1410783-16-2

1-(3-methoxy)-2...

N-(3-methoxyphenyl)naphthalen-2-amine Structure

38369-73-2

N-(3-methoxyphe...

2-Aminodiphenyl Structure

90-41-5

2-Aminodiphenyl

Chlorobenzene Structure

108-90-7

Chlorobenzene

~72%

[1,1'-biphenyl]-2-amine,N-phenyl Structure

35887-50-4

[1,1'-biphenyl]...

2,6-diphenylaniline Structure

87666-57-7

2,6-diphenylaniline

4-Aminobiphenyl Structure

92-67-1

4-Aminobiphenyl

Chlorobenzene Structure

108-90-7

Chlorobenzene

~64%

N-Phenyl-4-biphenylamine Structure

32228-99-2

N-Phenyl-4-biph...

[1,1':3',1''-Terphenyl]-4'-amine Structure

63344-48-9

[1,1':3',1''-Te...

Diphenylamine Structure

122-39-4

Diphenylamine

Chlorobenzene Structure

108-90-7

Chlorobenzene

~0%

Triphenylamine Structure

603-34-9

Triphenylamine

[1,1'-biphenyl]-2-amine,N-phenyl Structure

35887-50-4

[1,1'-biphenyl]...

1,2,3,4-Tetrahydroquinoline Structure

635-46-1

1,2,3,4-Tetrahy...

Chlorobenzene Structure

108-90-7

Chlorobenzene

~14%

1-Phenyl-1,2,3,4-tetrahydroquinoline Structure

3297-76-5

1-Phenyl-1,2,3,...

8-phenyl-1,2,3,4-tetrahydro-quinoline Structure

60640-18-8

8-phenyl-1,2,3,...

Chlorobenzene Structure

108-90-7

Chlorobenzene

Naphthalen-2-amine Structure

91-59-8

Naphthalen-2-amine

~0%

N-Phenyl-2-naphthylamine Structure

135-88-6

N-Phenyl-2-naph...

2-Amino-1-phenylnaphthalene Structure

29601-75-0

2-Amino-1-pheny...

ZR DX1&1&1 Structure

769-92-6

ZR DX1&1&1

Chlorobenzene Structure

108-90-7

Chlorobenzene

~0%

5-(tert-Butyl)-[1,1'-biphenyl]-2-amine Structure

1410783-24-2

5-(tert-Butyl)-...

4-(tert-butyl)-N-phenylaniline Structure

4496-49-5

4-(tert-butyl)-...

3-(Trifluoromethyl)aniline Structure

98-16-8

3-(Trifluoromet...

Chlorobenzene Structure

108-90-7

Chlorobenzene

~0%

2-Ph-4-CF3-aniline Structure

917381-61-4

2-Ph-4-CF3-aniline

Benzenamine,N-phenyl-3-(trifluoromethyl)- Structure

101-23-5

Benzenamine,N-p...

Detail
1-Aminonaphthalene Structure

134-32-7

1-Aminonaphthalene

Chlorobenzene Structure

108-90-7

Chlorobenzene

~83%

2-phenylnaphthalen-1-amine Structure

23645-37-6

2-phenylnaphtha...


Home | MSDS/SDS Database Search | Journals | Product Classification | Biologically Active Compounds | Selling Leads | About Us | Disclaimer

Copyright © 2024 ChemSrc All Rights Reserved