TBHP-promoted and iodide-catalyzed synthesis of anhydrides via cross dehydrogenative coupling (CDC) of aldehydes

被引:6
作者
Singha, Raju [1 ,2 ]
Ghosh, Munmun [1 ]
Nuree, Yasin [1 ]
Ray, Jayanta K. [1 ]
机构
[1] Indian Inst Technol, Dept Chem, Kharagpur 721302, W Bengal, India
[2] Panskura Banamali Coll, Dept Chem, Panskura 721152, RS, India
关键词
TBHP; Iodide; Aldehyde; CDC; Anhydride; CARBOXYLIC-ACID ANHYDRIDES; CHLORIDES; EFFICIENT; MILD;
D O I
10.1016/j.tetlet.2016.02.036
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
We have successfully developed a transition metal free green methodology for the synthesis of carboxylic anhydrides from aldehydes via CDC pathway and have also demonstrated the reaction mechanism. The developed method has also been successfully applied for the synthesis of amides. (C) 2016 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1325 / 1327
页数:3
相关论文
共 26 条
[1]   A one-step procedure for the monoacylation of symmetrical 1,2-diols [J].
Clarke, PA ;
Kayaleh, NE ;
Smith, MA ;
Baker, JR ;
Bird, SJ ;
Chan, C .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (15) :5226-5231
[2]   ANHYDRIDE FORMATION WITH THIONYL CHLORIDE. SYNTHESIS OF DI- AND TRI-AMINO-ALCOHOLS FROM CORRESPONDING TRI- AND TETRA-CARBOXYLIC ACIDS [J].
EDWARDS, D .
JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1966, (19) :1734-&
[3]   METATHETICAL REACTIONS OF SILVER SALTS IN SOLUTION .1. THE SYNTHESIS OF ACYL TRIFLUOROACETATES [J].
FERRIS, AF ;
EMMONS, WD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1953, 75 (01) :232-233
[4]   PHASE MANAGED ORGANIC-SYNTHESIS .3. SYMMETRICAL ANHYDRIDES FROM CARBOXYLIC-ACIDS VIA POLYMER ASSISTED REACTION [J].
FIFE, WK ;
ZHANG, ZD .
TETRAHEDRON LETTERS, 1986, 27 (41) :4937-4940
[5]   ACTIVATION OF MIXED CARBOXYLIC ALPHA-BROMOTOLUOYL ANHYDRIDES BY SILVER TETRAFLUOROBORATE - SYNTHESIS OF ESTERS AND THIOL ESTERS [J].
FUKUOKA, S ;
TAKIMOTO, S ;
KATSUKI, T ;
YAMAGUCHI, M .
TETRAHEDRON LETTERS, 1987, 28 (40) :4711-4712
[6]   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 [J].
Hajipour, AR ;
Mazloumi, G .
SYNTHETIC COMMUNICATIONS, 2002, 32 (01) :23-30
[7]   A CONVENIENT METHOD FOR PREPARATION OF ACID ANHYDRIDES FROM METALLIC CARBOXYLATES [J].
HATA, T ;
TAJIMA, K ;
MUKAIYAM.T .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1968, 41 (11) :2746-+
[8]   Mild and efficient synthesis of carboxylic acid anhydrides from carboxylic acids and triazine coupling reagents [J].
Kaminski, ZJ ;
Kolesinska, B ;
Malgorzata, M .
SYNTHETIC COMMUNICATIONS, 2004, 34 (18) :3349-3358
[9]   Dehydration induced by intramolecular redox character of a stable allylidenetributylphosphorane [J].
Kawamura, Y ;
Sato, Y ;
Horie, T ;
Tsukayama, M .
TETRAHEDRON LETTERS, 1997, 38 (45) :7893-7896
[10]   Simple preparation of symmetrical carboxylic acid anhydrides by means of Na2CO3/SOCl2 [J].
Kazemi, F. ;
Kiasat, A. R. ;
Mombaini, B. .
SYNTHETIC COMMUNICATIONS, 2007, 37 (18) :3219-3223