Tetrahedron

Highly chemoselective coupling of allenylstannanes with organic iodides promoted by Pd (PPh 3) 4/LiCl: an efficient method for the synthesis of substituted allenes

CW Huang, M Shanmugasundaram, HM Chang…

Index: Huang, Chih-Wei; Shanmugasundaram, Muthian; Chang, Hao-Ming; Cheng, Chien-Hong Tetrahedron, 2003 , vol. 59, # 20 p. 3635 - 3641

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Citation Number: 53

Abstract

An efficient method for the preparation of various monosubstituted arylallenes, disubstituted allenes and alkenylallenes via palladium-catalyzed coupling of allenylstannanes with aryl iodides or alkenyl iodides is described. The coupling reaction was carried out in the presence of Pd (PPh3) 4 and LiCl using DMF as solvent. The possible role of LiCl in this coupling process is discussed based on the 119Sn NMR studies.

 Related Synthetic Route
1-Iodonaphthalene Structure

90-14-2

1-Iodonaphthalene

allenyltributyltin Structure

53915-69-8

allenyltributyltin

~95%

1-propa-1,2-dienylnaphthalene Structure

57188-70-2

1-propa-1,2-die...

3-Iodoanisole Structure

766-85-8

3-Iodoanisole

allenyltributyltin Structure

53915-69-8

allenyltributyltin

~92%

1-methoxy-3-propa-1,2-dienylbenzene Structure

70090-80-1

1-methoxy-3-pro...

4-Iodotoluene Structure

615-37-2

4-Iodotoluene

allenyltributyltin Structure

53915-69-8

allenyltributyltin

~79%

1-methyl-2-propa-1,2-dienylbenzene Structure

71345-82-9

1-methyl-2-prop...

1-Iodo-4-nitrobenzene Structure

636-98-6

1-Iodo-4-nitrob...

allenyltributyltin Structure

53915-69-8

allenyltributyltin

~61%

1-nitro-4-propa-1,2-dienylbenzene Structure

38319-12-9

1-nitro-4-propa...

1-Bromo-4-iodobenzene Structure

589-87-7

1-Bromo-4-iodob...

allenyltributyltin Structure

53915-69-8

allenyltributyltin

~93%

1-bromo-4-propa-1,2-dienylbenzene Structure

91028-07-8

1-bromo-4-propa...

4-Iodotoluene Structure

624-31-7

4-Iodotoluene

allenyltributyltin Structure

53915-69-8

allenyltributyltin

~79%

1-methyl-4-propa-1,2-dienylbenzene Structure

2749-96-4

1-methyl-4-prop...

1-Chloro-4-iodobenzene Structure

637-87-6

1-Chloro-4-iodo...

allenyltributyltin Structure

53915-69-8

allenyltributyltin

~91%

1-chloro-4-propa-1,2-dienylbenzene Structure

2749-98-6

1-chloro-4-prop...

iodoanisole Structure

529-28-2

iodoanisole

allenyltributyltin Structure

53915-69-8

allenyltributyltin

~94%

1-methoxy-2-propa-1,2-dienylbenzene Structure

73234-94-3

1-methoxy-2-pro...

4-Iodoanisole Structure

696-62-8

4-Iodoanisole

allenyltributyltin Structure

53915-69-8

allenyltributyltin

~98%

1-methoxy-4-propa-1,2-dienylbenzene Structure

2749-97-5

1-methoxy-4-pro...

Iodobenzene Structure

591-50-4

Iodobenzene

allenyltributyltin Structure

53915-69-8

allenyltributyltin

~81%

1-Phenylallene Structure

2327-99-3

1-Phenylallene


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