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

The Journal of Organic Chemistry

Organotin nucleophiles. 5. Palladium-catalyzed allylic propargylation with allenylstannane

E Keinan, M Peretz

Index: Keinan, Ehud; Peretz, Moshe Journal of Organic Chemistry, 1983 , vol. 48, # 26 p. 5302 - 5309

Full Text: HTML

Citation Number: 66

Abstract

Allenyltrialkylstannanes were found to react with various allylic acetates in the presence of catalytic amounts of Pd (PPhd4 under mild neutral conditions, providing a novel approach for obtaining the 1, 5-enyne carbon skeleton. The regioselectivity of propargylation depends largely on the electron-withdrawing properties of the substituents at the two ends of the allylic system: substitution occurs at the end of closer proximity to the more electronegative ...

Sodium cyanide Structure

Ethanoic anhydride Structure

Ethanoic anhydride

para-methyl cinnamaldehyde Structure

para-methyl cin...

~%

[1-cyano-3-(4-methylphenyl)prop-2-enyl] acetate Structure

[1-cyano-3-(4-m...

(2-Bromovinyl)benzene Structure

(2-Bromovinyl)b...

~%

acetic acid,1,5-diphenylpenta-1,4-dien-3-ol Structure

acetic acid,1,5...

Cinnamaldehyde Structure

~%

acetic acid,1,5-diphenylpenta-1,4-dien-3-ol Structure

acetic acid,1,5...

1,5-diphenylpenta-1,4-dien-3-ol Structure

1,5-diphenylpen...

Ethanoic anhydride Structure

Ethanoic anhydride

~%

acetic acid,1,5-diphenylpenta-1,4-dien-3-ol Structure

acetic acid,1,5...

Cinnamaldehyde Structure

Acetylene Structure

~%

1-Phenyl-1-penten-4-yn-3-ol Structure

1-Phenyl-1-pent...

1-Phenyl-1-penten-4-yn-3-ol Structure

1-Phenyl-1-pent...

~%

acetic acid,1-phenyl-5-trimethylsilylpent-1-en-4-yn-3-ol Structure

acetic acid,1-p...

Cinnamaldehyde Structure

~%

acetic acid,1-phenyl-5-trimethylsilylpent-1-en-4-yn-3-ol Structure

acetic acid,1-p...

Chlorotrimethylsilane Structure

Chlorotrimethyl...

(E)-1-phenylpent-1-en-4-yn-3-yl acetate Structure

(E)-1-phenylpen...

~%

acetic acid,1-phenyl-5-trimethylsilylpent-1-en-4-yn-3-ol Structure

acetic acid,1-p...

allenyltributyltin Structure

allenyltributyltin

acetic acid,1-phenyl-5-trimethylsilylpent-1-en-4-yn-3-ol Structure

acetic acid,1-p...

~51%

trimethyl(5-phenylocta-3,6,7-trien-1-ynyl)silane Structure

trimethyl(5-phe...

trimethyl-[3-(2-phenylethenyl)hexa-1,5-diynyl]silane Structure

trimethyl-[3-(2...

Detail

allenyltributyltin Structure

allenyltributyltin

acetic acid,1-phenyl-5-trimethylsilylpent-1-en-4-yn-3-ol Structure

acetic acid,1-p...

~6%

trimethyl(5-phenylocta-3,6,7-trien-1-ynyl)silane Structure

trimethyl(5-phe...

trimethyl-[3-(2-phenylethenyl)hexa-1,5-diynyl]silane Structure

trimethyl-[3-(2...

Detail

allenyltributyltin Structure

allenyltributyltin

acetic acid,1-phenyl-5-trimethylsilylpent-1-en-4-yn-3-ol Structure

acetic acid,1-p...

~10%

trimethyl(5-phenylocta-3,6,7-trien-1-ynyl)silane Structure

trimethyl(5-phe...

trimethyl-[3-(2-phenylethenyl)hexa-1,5-diynyl]silane Structure

trimethyl-[3-(2...

Detail

p-Chlorocinnamaldehyde Structure

p-Chlorocinnama...

Sodium cyanide Structure

Ethanoic anhydride Structure

Ethanoic anhydride

~%

[3-(4-chlorophenyl)-1-cyanoprop-2-enyl] acetate Structure

[3-(4-chlorophe...

(E)-cinnamyl acetate Structure

(E)-cinnamyl acetate

allenyltributyltin Structure

allenyltributyltin

~24%

[(E)-hex-1-en-5-ynyl]benzene Structure

[(E)-hex-1-en-5...

hexa-1,4,5-trienylbenzene Structure

hexa-1,4,5-trie...

allenyltributyltin Structure

allenyltributyltin

[1-cyano-3-(4-methylphenyl)prop-2-enyl] acetate Structure

[1-cyano-3-(4-m...

~33%

4-(4-methylphenyl)-3-butenenitrile Structure

4-(4-methylphen...

2-[2-(4-methylphenyl)ethenyl]pent-4-ynenitrile Structure

2-[2-(4-methylp...

[1-cyano-3-(4-methylphenyl)prop-2-enyl] acetate Structure

[1-cyano-3-(4-m...

~18%

4-(4-methylphenyl)-3-butenenitrile Structure

4-(4-methylphen...

2-[2-(4-methylphenyl)ethenyl]pent-4-ynenitrile Structure

2-[2-(4-methylp...

para-methyl cinnamaldehyde Structure

para-methyl cin...

~%

2-[2-(4-methylphenyl)ethenyl]pent-4-ynenitrile Structure

2-[2-(4-methylp...

trimethyl(prop-2-enyl)stannane Structure

trimethyl(prop-...

[1-cyano-3-(4-methylphenyl)prop-2-enyl] acetate Structure

[1-cyano-3-(4-m...

~18%

4-(4-methylphenyl)-3-butenenitrile Structure

4-(4-methylphen...

2-[2-(4-methylphenyl)ethenyl]pent-4-ynenitrile Structure

2-[2-(4-methylp...

trimethyl-[3-(2-phenylethenyl)hexa-1,5-diynyl]silane Structure

trimethyl-[3-(2...

~93%

3-ethynylhex-1-en-5-ynylbenzene Structure

3-ethynylhex-1-...

Tetraallyltin Structure

acetic acid,1-phenylhex-1-en-4-yn-3-ol Structure

acetic acid,1-p...

~67%

3-prop-1-ynylhexa-1,5-dienylbenzene Structure

3-prop-1-ynylhe...

4-phenylnona-1,5-dien-7-yne Structure

4-phenylnona-1,...

Detail

4-Methoxycinnamaldehyde Structure

4-Methoxycinnam...

Trimethylsilyl cyanide Structure

Trimethylsilyl ...

Ethanoic anhydride Structure

Ethanoic anhydride

~%

[1-cyano-3-(4-methoxyphenyl)prop-2-enyl] acetate Structure

[1-cyano-3-(4-m...

[1-cyano-3-(4-methoxyphenyl)prop-2-enyl] acetate Structure

[1-cyano-3-(4-m...

~23%

4-(4-methoxyphenyl)but-3-enenitrile Structure

4-(4-methoxyphe...

2-[2-(4-methoxyphenyl)ethenyl]pent-4-ynenitrile Structure

2-[2-(4-methoxy...

4-Methoxycinnamaldehyde Structure

4-Methoxycinnam...

~%

2-[2-(4-methoxyphenyl)ethenyl]pent-4-ynenitrile Structure

2-[2-(4-methoxy...

allenyltributyltin Structure

allenyltributyltin

[1-cyano-3-(4-methoxyphenyl)prop-2-enyl] acetate Structure

[1-cyano-3-(4-m...

~23%

4-(4-methoxyphenyl)but-3-enenitrile Structure

4-(4-methoxyphe...

2-[2-(4-methoxyphenyl)ethenyl]pent-4-ynenitrile Structure

2-[2-(4-methoxy...

4-Fluorobenzaldehyde Structure

4-Fluorobenzaldehyde

~%

1-fluoro-4-(1-phenylhex-1-en-5-yn-3-yl)benzene Structure

1-fluoro-4-(1-p...

trans-1-(4-fluorophenyl)-3-phenylprop-2-en-1-ol Structure

trans-1-(4-fluo...

~%

1-fluoro-4-(1-phenylhex-1-en-5-yn-3-yl)benzene Structure

1-fluoro-4-(1-p...

Acetophenone Structure

~%

1-fluoro-4-(1-phenylhex-1-en-5-yn-3-yl)benzene Structure

1-fluoro-4-(1-p...

[1-cyano-3-(4-methoxyphenyl)prop-2-enyl] acetate Structure

[1-cyano-3-(4-m...

~23%

4-(4-methoxyphenyl)but-3-enenitrile Structure

4-(4-methoxyphe...

2-[2-(4-methoxyphenyl)ethenyl]pent-4-ynenitrile Structure

2-[2-(4-methoxy...

4-Methoxycinnamaldehyde Structure

4-Methoxycinnam...

~%

4-(4-methoxyphenyl)but-3-enenitrile Structure

4-(4-methoxyphe...

allenyltributyltin Structure

allenyltributyltin

[1-cyano-3-(4-methoxyphenyl)prop-2-enyl] acetate Structure

[1-cyano-3-(4-m...

~22%

4-(4-methoxyphenyl)but-3-enenitrile Structure

4-(4-methoxyphe...

2-[2-(4-methoxyphenyl)ethenyl]pent-4-ynenitrile Structure

2-[2-(4-methoxy...

[3-(4-chlorophenyl)-1-cyanoprop-2-enyl] acetate Structure

[3-(4-chlorophe...

~14%

4-(4-chlorophenyl)but-3-enenitrile Structure

4-(4-chlorophen...

2-[2-(4-chlorophenyl)ethenyl]pent-4-ynenitrile Structure

2-[2-(4-chlorop...

p-Chlorocinnamaldehyde Structure

p-Chlorocinnama...

~%

2-[2-(4-chlorophenyl)ethenyl]pent-4-ynenitrile Structure

2-[2-(4-chlorop...

allenyltributyltin Structure

allenyltributyltin

[3-(4-chlorophenyl)-1-cyanoprop-2-enyl] acetate Structure

[3-(4-chlorophe...

~15%

4-(4-chlorophenyl)but-3-enenitrile Structure

4-(4-chlorophen...

2-[2-(4-chlorophenyl)ethenyl]pent-4-ynenitrile Structure

2-[2-(4-chlorop...

4-Bromobenzaldehyde Structure

4-Bromobenzaldehyde

~%

1-bromo-4-(1-phenylhex-1-en-5-yn-3-yl)benzene Structure

1-bromo-4-(1-ph...

Acetophenone Structure

~%

1-bromo-4-(1-phenylhex-1-en-5-yn-3-yl)benzene Structure

1-bromo-4-(1-ph...

2-Propenal, 3- (4-nitrophenyl)- Structure

2-Propenal, 3- ...

Sodium cyanide Structure

Ethanoic anhydride Structure

Ethanoic anhydride

~%

[1-cyano-3-(4-nitrophenyl)prop-2-enyl] acetate Structure

[1-cyano-3-(4-n...

Cinnamaldehyde Structure

~%

acetic acid,1-phenylhex-1-en-4-yn-3-ol Structure

acetic acid,1-p...

(E)-1-phenyl-1-hexen-4-yn-3-ol Structure

(E)-1-phenyl-1-...

Ethanoic anhydride Structure

Ethanoic anhydride

~%

acetic acid,1-phenylhex-1-en-4-yn-3-ol Structure

acetic acid,1-p...

allenyltributyltin Structure

allenyltributyltin

acetic acid,1-phenylhex-1-en-4-yn-3-ol Structure

acetic acid,1-p...

~%

3-prop-2-ynylhex-1-en-4-ynylbenzene Structure

3-prop-2-ynylhe...

4-phenylnona-1,7-diyn-5-ene Structure

4-phenylnona-1,...

Detail

p-Tolualdehyde Structure

~%

1-methyl-4-(1-phenylhex-1-en-5-yn-3-yl)benzene Structure

1-methyl-4-(1-p...

(E)-1-(4-methylphenyl)-3-phenyl-2-propen-1-ol Structure

(E)-1-(4-methyl...

~%

1-methyl-4-(1-phenylhex-1-en-5-yn-3-yl)benzene Structure

1-methyl-4-(1-p...

Acetophenone Structure

~%

1-methyl-4-(1-phenylhex-1-en-5-yn-3-yl)benzene Structure

1-methyl-4-(1-p...