Synthesis of Symmetrical Carboxylic Acid Anhydrides from Acyl Chlorides in the Presence of In Metal and DMF

Many of these methods, however, suffer from drawbacks including use of ex-pensive and/or toxic reagents, low yields, tedious workup pro-cedures, harsh reaction conditions and incompatibility with poly-functionalized substrates. Therefore, mild and efficient methods for preparing carboxylic acid anhydrides are still in great demand.Organic reactions employing indium metal have gained considerable attention because indium-mediated reactions show high reactivity and unique properties in organic or aqueous medium.

[1]  J. F. Wolfe,et al.  The synthesis of carboxylic acids and esters and their derivatives , 2010 .

[2]  F. Chemla,et al.  Zinc(0)/dimethylformamide-mediated synthesis of symmetrical carboxylic anhydrides from acid chlorides , 2008 .

[3]  A. Kiasat,et al.  Simple Preparation of Symmetrical Carboxylic Acid Anhydrides by Means of Na2CO3/SOCl2 , 2007 .

[4]  J. Kim,et al.  Highly selective catalytic Friedel–Crafts acylation and sulfonylation of activated aromatic compounds using indium metal , 2006 .

[5]  W. Chavasiri,et al.  Indium-mediated mild and efficient one-pot synthesis of alkyl phenyl selenides , 2005 .

[6]  D. Jang,et al.  Indium-mediated mild and facile method for the synthesis of amides , 2004 .

[7]  B. Kolesińska,et al.  Mild and Efficient Synthesis of Carboxylic Acid Anhydrides from Carboxylic Acids and Triazine Coupling Reagents , 2004 .

[8]  J. Kim,et al.  Indium promoted-convenient method for acylation of alcohols with acyl chlorides , 2003 .

[9]  J. Baker,et al.  A one-step procedure for the monoacylation of symmetrical 1,2-diols. , 2002, The Journal of organic chemistry.

[10]  A. Hajipour,et al.  AN EFFICIENT AND SIMPLE PROCEDURE FOR PREPARATION OF ESTERS AND ANHYDRIDES FROM ACID CHLORIDES IN THE PRESENCE OF 1,4-DIAZABICYCLO[2.2.2]OCTANE (DABCO) UNDER SOLVENT-FREE CONDITIONS , 2002 .

[11]  C. Kappe,et al.  The effect of microwave irradiation on carbodiimide-mediated esterifications on solid support , 2001 .

[12]  J. Kim,et al.  A CONVENIENT METHOD FOR SYNTHESIS OF SYMMETRICAL ACID ANHYDRIDES FROM CARBOXYLIC ACIDS WITH TRICHLOROACETONITRILE AND TRIPHENYLPHOSPHINE , 2001 .

[13]  A. Barrett,et al.  Nucleophilic Substitution Reactions of (Alkoxymethylene)dimethylammonium Chloride. , 1998, The Journal of organic chemistry.

[14]  Y. Kawamura,et al.  DEHYDRATION INDUCED BY INTRAMOLECULAR REDOX CHARACTER OF A STABLE ALLYLIDENETRIBUTYLPHOSPHORANE , 1997 .

[15]  Chao‐Jun Li Aqueous Barbier-Grignard Type Reaction: Scope, Mechanism, and Synthetic Applications , 1996 .

[16]  S. Mobashery,et al.  A Convenient Triphosgene-Mediated Synthesis of Symmetric Carboxylic Acid Anhydrides , 1994 .

[17]  Chao-Jun Li Organic reactions in aqueous media - with a focus on carbon-carbon bond formation , 1993 .

[18]  Y. Butsugan,et al.  Indium in organic synthesis: indium-mediated allylation of carbonyl compounds , 1988 .

[19]  D. Seebach,et al.  Aminierende reduktive Kupplung aromatischer Aldehyde mit niervalenten Titan‐Reagenzien zu 1,2‐Diarylethylendiaminen , 1987 .

[20]  Y. Kita,et al.  Facile and efficient syntheses of carboxylic anhydrides and amides using (trimethylsilyl)ethoxyacetylene , 1986 .

[21]  W. Nakanishi,et al.  Reaction of 2-(methylseleno)- and 2-(phenylseleno)benzoic acids and their derivatives with tert-butyl hydroperoxide. Neighboring selenium participation and facile formation of cyclic selenuranes and a selenurane oxide , 1982 .

[22]  T. Katsuki,et al.  Synthesis of Thiol Esters by Carboxylic Trichlorobenzoic Anhydrides , 1981 .

[23]  H. Rinderknecht,et al.  Eine einfache neue Synthese für Säureanhydride , 1964 .

[24]  H. Khorana,et al.  Studies on Polynucleotides. XX.1Amino Acid Acceptor Ribonucleic Acids (1). The Synthesis and Properties of 2″ (or 3″)-O-(DL-Phenylalanyl)-adenosine, 2″ (or 3″)-O-(DL-Phenylalanyl)-uridine and Related Compounds2 , 1963 .

[25]  H. H. Bosshard,et al.  Eine Methode zur katalysierten Herstellung von Carbonsäure- und Sulfosäure-chloriden mit Thionylchlorid† , 1959 .