Oxidative Decarboxylation of 2-Aryl Carboxylic Acids Using (Diacetoxyiodo)benzene for Preparation of Aryl Aldehydes, Ketones, and Nitriles

被引：23

作者：

Telvekar, Vikas N. ^{[1
]}

Sasane, Kulbhushan A. ^{[1
]}

机构：

[1] Inst Chem Technol, Dept Pharmaceut Sci & Technol, Bombay 400019, Maharashtra, India

来源：

SYNLETT | 2010年 / 18期

关键词：

(diacetoxyiodo)benzene; decarboxylation; aldehydes; ketones; nitriles; AMINO-ACIDS; HIGHLY EFFICIENT; ALPHA-AMINO; PERIODATE;

D O I：

10.1055/s-0030-1258812

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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

引用

页码：2778 / 2780

页数：3

共 22 条

[1] OXIDATIVE DECARBOXYLATION OF ALPHA-HYDROXY CARBOXYLIC-ACIDS WITH N-IODOSUCCINIMIDE [J].

BEEBE, TR ;

ADKINS, RL ;

BELCHER, AI ;

CHOY, T ;

FULLER, AE ;

MORGAN, VL ;

SENCHEREY, BB ;

RUSSELL, LJ ;

YATES, SW .

JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (15) :3006-3008

[2] On the oxidation of amino-acids and of related substances with chloramine-T. [J].

Dakin, HD .

BIOCHEMICAL JOURNAL, 1917, 11 (02) :79-95

[3] The oxidation of amino acids with sodium hypobromite [J].

Friedman, AH ;

Morgulis, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1936, 58 :909-913

[4] Conversion of α-amino acids into nitriles by oxidative decarboxylation with trichloroisocyanuric acid [J].

Hiegel, GA ;

Lewis, JC ;

Bae, JW .

SYNTHETIC COMMUNICATIONS, 2004, 34 (19) :3449-3453

[5] Diacetoxyiodobenzene-mediated oxidative addition of 1,3-dicarbonyl compounds to olefins: an efficient one-pot synthesis of 2,3-dihydrofuran derivatives [J].

Karade, NN ;

Shirodkar, SG ;

Patil, MN ;

Potrekar, RA ;

Karade, HN .

TETRAHEDRON LETTERS, 2003, 44 (35) :6729-6731

[6] A NOVEL AND FACILE SYNTHESIS OF TETRAACYLBENZENES [J].

KOTALI, A .

TETRAHEDRON LETTERS, 1994, 35 (36) :6753-6754

[7] Synthesis and electron impact mass spectra of 3-substituted 2-acylaminoindazoles [J].

Kotali, A ;

Harris, PA .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1996, 33 (03) :605-606

[8] Polystyrene-bound Mn(T4PyP): A highly efficient and reusable catalyst for biomimetic oxidative decarboxylation of carboxylic acids with sodium periodate [J].

Moghadam, Majid ;

Tangestaninejad, Shahram ;

Mirkhani, Valiollah ;

Mohammadpoor-baltork, Iraj ;

Sirjanian, Narges ;

Parand, Somayeh .

BIOORGANIC & MEDICINAL CHEMISTRY, 2009, 17 (09) :3394-3398

[9] CLEAVAGE OF NH2 TERMINAL TYROSYL PEPTIDE-BONDS USING HYPERVALENT IODINE [J].

MORIARTY, RM ;

SULTANA, M ;

KU, YY .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1985, (14) :974-975

[10]

NAKAGAWA K, 1964, CHEM PHARM BULL, V12, P403

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