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

Tetrahedron

Tetraphosphine/palladium catalysed Suzuki cross-coupling reactions of aryl halides with alkylboronic acids

I Kondolff, H Doucet, M Santelli

Index: Kondolff, Isabelle; Doucet, Henri; Santelli, Maurice Tetrahedron, 2004 , vol. 60, # 17 p. 3813 - 3818

Full Text: HTML

Citation Number: 48

Abstract

Through the use of [PdCl (C3H5)] 2/cis, cis, cis-1, 2, 3, 4-tetrakis (diphenylphosphinomethyl) cyclopentane as a catalyst, a range of aryl bromides and chlorides undergoes Suzuki cross- coupling with alkylboronic acids in good yields. Several alkyl substituents such as ethyl, n- butyl, n-octyl, isobutyl or 2, 2-dimethylpropyl on the alkylboronic acids have been successfully used. The functional group tolerance on the aryl halide is remarkable; ...

1-Butaneboronic acid Structure

1-Butaneboronic acid

9-Bromoanthracene Structure

9-Bromoanthracene

~90%

9-Butylanthracene Structure

9-Butylanthracene

1-Butaneboronic acid Structure

1-Butaneboronic acid

1-Bromonaphthalene Structure

1-Bromonaphthalene

~91%

1-Butylnaphthalene Structure

1-Butylnaphthalene

Octylboronic acid Structure

Octylboronic acid

4-Bromobenzaldehyde Structure

4-Bromobenzaldehyde

~74%

4-Octylbenzaldehyde Structure

4-Octylbenzaldehyde

3-Bromopyridine Structure

3-Bromopyridine

Octylboronic acid Structure

Octylboronic acid

~86%

3-Octylpyridine Structure

3-Octylpyridine

1-Butaneboronic acid Structure

1-Butaneboronic acid

4-Bromobenzophenone Structure

4-Bromobenzophenone

~95%

4-N-BUTYLBENZOPHENONE Structure

4-N-BUTYLBENZOP...

1-Butaneboronic acid Structure

1-Butaneboronic acid

1-Bromo-4-nitrobenzene Structure

1-Bromo-4-nitro...

~83%

1-Butyl-4-nitrobenzene Structure

1-Butyl-4-nitro...

1-Butaneboronic acid Structure

1-Butaneboronic acid

4-Chloronitrobenzene Structure

4-Chloronitrobenzene

~73%

1-Butyl-4-nitrobenzene Structure

1-Butyl-4-nitro...

Ethylboronic acid Structure

Ethylboronic acid

2-Bromobenzaldehyde Structure

2-Bromobenzaldehyde

~58%

2-Ethylbenzaldehyde Structure

2-Ethylbenzaldehyde

Propylboronic acid Structure

Propylboronic acid

1-(4-Bromophenyl)ethanone Structure

1-(4-Bromopheny...

~75%

p-Propylacetophenone Structure

p-Propylacetophenone

4-Bromopyridine Structure

4-Bromopyridine

Octylboronic acid Structure

Octylboronic acid

~80%

4-Octylpyridine Structure

4-Octylpyridine

Ethylboronic acid Structure

Ethylboronic acid

1-(4-Bromophenyl)ethanone Structure

1-(4-Bromopheny...

~90%

P-ETHYLACETOPHENONE Structure

P-ETHYLACETOPHENONE

(2-Phenylethyl)boronic acid Structure

(2-Phenylethyl)...

1-(4-Bromophenyl)ethanone Structure

1-(4-Bromopheny...

~96%

1-[4-(2-phenylethyl)phenyl]ethanone Structure

1-[4-(2-phenyle...

1-Butaneboronic acid Structure

1-Butaneboronic acid

4-Bromobenzaldehyde Structure

4-Bromobenzaldehyde

~84%

4-Butylbenzaldehyde Structure

4-Butylbenzaldehyde

1-Butaneboronic acid Structure

1-Butaneboronic acid

1-Bromo-2-nitrobenzene Structure

1-Bromo-2-nitro...

~80%

1-Butyl-2-nitrobenzene Structure

1-Butyl-2-nitro...

Octylboronic acid Structure

Octylboronic acid

1-(4-Bromophenyl)ethanone Structure

1-(4-Bromopheny...

~94%

p-Octylacetophenone Structure

p-Octylacetophenone

Chloroquinoline Structure

Chloroquinoline

1-Butaneboronic acid Structure

1-Butaneboronic acid

~74%

2-butylquinoline Structure

2-butylquinoline

biquinoline Structure

1-Butaneboronic acid Structure

1-Butaneboronic acid

2-Bromobenzonitrile Structure

2-Bromobenzonitrile

~91%

2-butylbenzonitrile Structure

2-butylbenzonitrile

2-Bromopyridine Structure

2-Bromopyridine

Octylboronic acid Structure

Octylboronic acid

~50%

2-Octylpyridine Structure

2-Octylpyridine

1-Butaneboronic acid Structure

1-Butaneboronic acid

2-Bromobiphenyl Structure

2-Bromobiphenyl

~93%

2-Butylbiphenyl Structure

2-Butylbiphenyl

Photochemical generation of radical anions via organolithium...

[Winkler,H.J.S. et al. Journal of Organic Chemistry, 1967 , vol. 32, p. 1700 - 1706]