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

Alkylation of pyridine in free radical chain reactions utilizing alkylmercurials

GA Russell, D Guo, RK Khanna

Index: Russell, Glen A.; Guo, Deliang; Khanna, Rajive K. Journal of Organic Chemistry, 1985 , vol. 50, # 18 p. 3423 - 3425

Full Text: HTML

Citation Number: 18

Abstract

Summary: Pyridines or N, N, N', N'-tetramethyl-pphenylenediamine will undergo a photostimulated free radical chain reaction with alkylmercury halides or carboxylates, yielding ring alkylated substitution products. Alkene mercuration products (R'CH (Y) CH (R2) HgX with Y= HO, RO, CH3CONH; X= C1, CH3C02, CF3C02) can be used without isolation for the alkylation reaction.

2-Chloropyridine Structure

2-Chloropyridine

tert-butyl(chloro)mercury Structure

tert-butyl(chlo...

~%

4-tert-butyl-2-chloropyridine Structure

4-tert-butyl-2-...

2-tert-butyl-6-chloropyridine Structure

2-tert-butyl-6-...

Methyl nicotinate Structure

Methyl nicotinate

tert-butyl(chloro)mercury Structure

tert-butyl(chlo...

~75%

methyl 6-tert-butylpyridine-3-carboxylate Structure

methyl 6-tert-b...

Pyridine Structure

chloro(cyclohexyl)mercury Structure

chloro(cyclohex...

~%

2-cyclohexylpyridine Structure

2-cyclohexylpyridine

4-cyclohexylpyridine Structure

4-cyclohexylpyridine

Pyridine Structure

tert-butyl(chloro)mercury Structure

tert-butyl(chlo...

~%

4-Tert-Butylpyridine Structure

4-Tert-Butylpyridine

2-tert-butylpyridine Structure

2-tert-butylpyridine

Pyridine Structure

chloro(2,2-dimethylpropyl)mercury Structure

chloro(2,2-dime...

~%

4-(2,2-dimethyl-propyl)-pyridine Structure

4-(2,2-dimethyl...

2-(2,2-dimethylpropyl)pyridine Structure

2-(2,2-dimethyl...

Pyridine Structure

Methanol Structure

ethene Structure

~%

4-(2-methoxyethyl)pyridine Structure

4-(2-methoxyeth...

Detail

Pyridine Structure

chloro(hexyl)mercury Structure

chloro(hexyl)mercury

~%

2-n-Hexylpyridine Structure

2-n-Hexylpyridine

4-Hexylpyridine Structure

4-Hexylpyridine

Pyridine Structure

chloro(cyclohexyl)mercury Structure

chloro(cyclohex...

~%

2-cyclohexylpyridine Structure

2-cyclohexylpyridine

4-cyclohexylpyridine Structure

4-cyclohexylpyridine

3-Phenylpyridine Structure

3-Phenylpyridine

tert-butyl(chloro)mercury Structure

tert-butyl(chlo...

~61%

2-tert-butyl-5-phenylpyridine Structure

2-tert-butyl-5-...

3-Mepy Structure

tert-butyl(chloro)mercury Structure

tert-butyl(chlo...

~90%

2-tert-butyl-5-methylpyridine Structure

2-tert-butyl-5-...

Pyridine Structure

tert-butyl(chloro)mercury Structure

tert-butyl(chlo...

~%

4-Tert-Butylpyridine Structure

4-Tert-Butylpyridine

2-tert-butylpyridine Structure

2-tert-butylpyridine

Pyridine Structure

n-BUTYLMERCURIC CHLORIDE Structure

n-BUTYLMERCURIC...

~%

2-Butylpyridine Structure

2-Butylpyridine

4-BUTYL PYRIDINE Structure

4-BUTYL PYRIDINE

Benzo[d]thiazole Structure

Benzo[d]thiazole

tert-butyl(chloro)mercury Structure

tert-butyl(chlo...

~70%

Benzothiazole,2-(1,1-dimethylethyl)- Structure

Benzothiazole,2...

2-Phenylpyridine Structure

2-Phenylpyridine

tert-butyl(chloro)mercury Structure

tert-butyl(chlo...

~%

4-tert-butyl-2-phenylpyridine Structure

4-tert-butyl-2-...

2-tert-butyl-6-phenylpyridine Structure

2-tert-butyl-6-...

Intra-and Intermolecular C–H Activation by Bis (phenolate) p...

[Fu, Ross; Bercaw, John E.; Labinger, Jay A. Organometallics, 2011 , vol. 30, # 24 p. 6751 - 6765]