Pd??Catalyzed Tandem Chemoselective Synthesis of 2??Arylbenzofurans using Threefold Arylating Triarylbismuth Reagents

…, DN Jadhav, P Dasgupta

Index: Rao, Maddali L. N.; Jadhav, Deepak N.; Dasgupta, Priyabrata European Journal of Organic Chemistry, 2013 , # 4 p. 781 - 788

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Citation Number: 1

Abstract

Abstract A tandem chemoselective synthesis of 2-arylbenzofurans was accomplished from o- hydroxy-gem-(dibromovinyl) benzenes and BiAr 3 reagents under palladium-catalyzed conditions. This unique and synthetically valuable strategy proceeds through three consecutive coupling reactions involving triarylbismuth reagents and provides 2- arylbenzofuran products in high yields.

 Related Synthetic Route
N/A Structure

1191415-07-2

N/A

Tris(4-methylphenyl)bismuthine Structure

5142-75-6

Tris(4-methylph...

~0%

BI-P-TOLYL Structure

613-33-2

BI-P-TOLYL

N/A Structure

22772-25-4

N/A

Tris(4-methylphenyl)bismuthine Structure

5142-75-6

Tris(4-methylph...

Phenol, 2-(2,2-dibromoethenyl)- Structure

91703-34-3

Phenol, 2-(2,2-...

~0%

N/A Structure

25664-48-6

N/A

BI-P-TOLYL Structure

613-33-2

BI-P-TOLYL

Tris(4-methylphenyl)bismuthine Structure

5142-75-6

Tris(4-methylph...

N/A Structure

95186-48-4

N/A

~0%

5-Chloro-2-(p-tolyl)benzofuran Structure

22772-26-5

5-Chloro-2-(p-t...

BI-P-TOLYL Structure

613-33-2

BI-P-TOLYL

tris(4-methoxyphenyl)bismuth Structure

33397-21-6

tris(4-methoxyp...

N/A Structure

95186-48-4

N/A

~0%

5-Chloro-2-(4-methoxy-phenyl)-benzofuran Structure

24472-98-8

5-Chloro-2-(4-m...

4,4'-Dimethoxybiphenyl Structure

2132-80-1

4,4'-Dimethoxyb...

tris(4-methoxyphenyl)bismuth Structure

33397-21-6

tris(4-methoxyp...

Phenol, 2-(2,2-dibromoethenyl)- Structure

91703-34-3

Phenol, 2-(2,2-...

~0%

2-(4-methoxyphenyl)benzofuran Structure

19234-04-9

2-(4-methoxyphe...

4,4'-Dimethoxybiphenyl Structure

2132-80-1

4,4'-Dimethoxyb...

tris(4-ethoxyphenyl)bismuthane Structure

90591-48-3

tris(4-ethoxyph...

N/A Structure

95186-48-4

N/A

~0%

4,4'-Diethoxybiphenyl Structure

7168-54-9

4,4'-Diethoxybi...

N/A Structure

1448818-01-6

N/A

N/A Structure

1191415-07-2

N/A

tris(4-ethoxyphenyl)bismuthane Structure

90591-48-3

tris(4-ethoxyph...

~0%

4,4'-Diethoxybiphenyl Structure

7168-54-9

4,4'-Diethoxybi...

5-bromo-2-(4-ethoxyphenyl)benzofuran Structure

1374787-42-4

5-bromo-2-(4-et...

tris(4-ethoxyphenyl)bismuthane Structure

90591-48-3

tris(4-ethoxyph...

Phenol, 2-(2,2-dibromoethenyl)- Structure

91703-34-3

Phenol, 2-(2,2-...

~0%

4,4'-Diethoxybiphenyl Structure

7168-54-9

4,4'-Diethoxybi...

N/A Structure

1374787-32-2

N/A

Triphenylbismuth Structure

603-33-8

Triphenylbismuth

Phenol, 2-(2,2-dibromoethenyl)- Structure

91703-34-3

Phenol, 2-(2,2-...

~73%

2-Phenylbenzofuran Structure

1839-72-1

2-Phenylbenzofuran

Biphenyl Structure

92-52-4

Biphenyl

Triphenylbismuth Structure

603-33-8

Triphenylbismuth

Phenol, 2-(2,2-dibromoethenyl)- Structure

91703-34-3

Phenol, 2-(2,2-...

~%

2-Bromo-1-benzofuran Structure

54008-77-4

2-Bromo-1-benzofuran

2-Phenylbenzofuran Structure

1839-72-1

2-Phenylbenzofuran

Detail
3-(2,2-dibromovinyl)biphenyl-4-ol Structure

1448818-05-0

3-(2,2-dibromov...

Triphenylbismuth Structure

603-33-8

Triphenylbismuth

~57%

Biphenyl Structure

92-52-4

Biphenyl

2,5-diphenyl-1-benzofuran Structure

121045-39-4

2,5-diphenyl-1-...

N/A Structure

95149-16-9

N/A

N/A Structure

1191415-07-2

N/A

~0%

1,1'-Biphenyl, 3,3'-dimethoxy- Structure

6161-50-8

1,1'-Biphenyl, ...

N/A Structure

1448818-00-5

N/A

N/A Structure

95149-16-9

N/A

N/A Structure

95186-48-4

N/A

~0%

1,1'-Biphenyl, 3,3'-dimethoxy- Structure

6161-50-8

1,1'-Biphenyl, ...

N/A Structure

1448818-04-9

N/A

N/A Structure

95149-16-9

N/A

Phenol, 2-(2,2-dibromoethenyl)- Structure

91703-34-3

Phenol, 2-(2,2-...

~0%

2-(3'-methoxyphenyl)benzofuran Structure

26870-34-8

2-(3'-methoxyph...

1,1'-Biphenyl, 3,3'-dimethoxy- Structure

6161-50-8

1,1'-Biphenyl, ...

N/A Structure

124066-73-5

N/A

Phenol, 2-(2,2-dibromoethenyl)- Structure

91703-34-3

Phenol, 2-(2,2-...

~0%

2-thiophen-2-yl-1-benzofuran Structure

65246-50-6

2-thiophen-2-yl...

2,2'-Bithiophene Structure

492-97-7

2,2'-Bithiophene

tris(4-chlorophenyl)bismuthane Structure

5575-51-9

tris(4-chloroph...

Phenol, 2-(2,2-dibromoethenyl)- Structure

91703-34-3

Phenol, 2-(2,2-...

~62%

2-(4-Chlorophenyl)benzofuran Structure

39195-66-9

2-(4-Chlorophen...

4,4'-PCB Structure

2050-68-2

4,4'-PCB

N/A Structure

124066-73-5

N/A

Phenol, 2-(2,2-dibromoethenyl)- Structure

91703-34-3

Phenol, 2-(2,2-...

~51%

2-thiophen-2-yl-1-benzofuran Structure

65246-50-6

2-thiophen-2-yl...

2,2'-Bithiophene Structure

492-97-7

2,2'-Bithiophene

(3-(2,2-dibromovinyl)-4-hydroxyphenyl)(phenyl)methanone Structure

1448818-07-2

(3-(2,2-dibromo...

Triphenylbismuth Structure

603-33-8

Triphenylbismuth

~72%

1-(2-phenyl-1-benzofuran-5-yl)ethanone Structure

121045-41-8

1-(2-phenyl-1-b...

Biphenyl Structure

92-52-4

Biphenyl

N/A Structure

1321985-62-9

N/A

Triphenylbismuth Structure

603-33-8

Triphenylbismuth

~75%

Biphenyl Structure

92-52-4

Biphenyl

5,7-dichloro-2-phenyl-1-benzofuran Structure

18761-38-1

5,7-dichloro-2-...


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