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DOI: 10.1055/s-0030-1258812
Oxidative Decarboxylation of 2-Aryl Carboxylic Acids Using (Diacetoxyiodo)benzene for Preparation of Aryl Aldehydes, Ketones, and Nitriles
Publication History
Publication Date:
08 October 2010 (online)

Abstract
A novel synthetic application of the hypervalent iodine reagent, (diacetoxyiodo)benzene, and catalytic amount of sodium azide in acetonitrile for oxidative decarboxylation of 2-aryl carboxylic acids into corresponding aldehydes, ketones, and nitriles at room temperature is described. The advantages of this protocol are shorter reaction times and mild reaction conditions to obtain moderate to good yields
Key words
(diacetoxyiodo)benzene - decarboxylation - aldehydes - ketones - nitriles
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References and Notes
Representative
Procedure for Decarboxylation of Phenylacetic Acid (Table 1, Entry
1)
(Diacetoxyiodo)benzene (1.5 equiv) and NaN3 (0.12
equiv) in MeCN (10 mL) were stirred at 0 ˚C for 2 min,
then phenyl acetic acid (1 equiv) was added to the stirred solution.
The reaction mixture was allowed to come at r.t. and stirring continued
until completion of reaction (TLC), when it was quenched with H2O
(25 mL) and extracted with CHCl3 (3 × 10
mL). The combined organic layers were washed with dilute NaHCO3 (20
mL), followed by H2O (3 × 20
mL), dried over Na2SO4, and concentrated in
vacuo. The residue was purified by column chromatography on silica
gel (hexane-EtOAc = 9:1) to
yield benzaldehyde (88%) as a colorless liquid.
Representative
Procedure for Decarboxylation of α-Amino(phenyl)acetic
Acid (Table 1, Entry 13)
(Diacetoxyiodo)benzene (1.5
equiv) and NaN3 (0.12 equiv) in MeCN (10 mL) were stirred
at r.t. for 2 min, then α-amino-(phenyl)acetic acid (1
equiv) was added to the stirred solution. Stirring was continued
until completion of reaction (TLC), when it was quenched with H2O
(25 mL) and worked up as mentioned above to yield benzonitrile (90%)
as a colorless liquid; bp 188 ˚C. IR (neat): 2230,
2256, 2178, 1682, 1572, 1492 cm-¹. ¹³C
NMR (75 MHz, CDCl3): δ = 132.84, 132.10,
129.21, 118.82, 112.41.