An efficient method for one-carbon elongation of aryl aldehydes via their dibromoalkene derivatives

被引:75
作者
Huh, DH [1 ]
Jeong, JS [1 ]
Lee, HB [1 ]
Ryu, H [1 ]
Kim, YG [1 ]
机构
[1] Seoul Natl Univ, Coll Engn, Sch Chem Engn, Seoul 151744, South Korea
关键词
one-carbon elongation; aryl-1,1-dibromoalkene; aryl aldehyde; aryl acetamide; aryl acetic acid;
D O I
10.1016/S0040-4020(02)01324-8
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Various aryl aldehydes were efficiently converted into one-carbon extended aryl acetamides or aryl acetic acids through the reaction of their dibromoalkene derivatives with pyrrolidine in the presence of water under very mild conditions. (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:9925 / 9932
页数:8
相关论文
共 37 条
[1]  
[Anonymous], COMPREHENSIVE ORGANI
[2]   A highly stereoselective synthesis of D-erythrose derivatives by one-carbon homologation of 2,3-O-isopropylidene-D-glyceraldehyde with (R)-methyl p-tolyl sulfoxide [J].
Arroyo-Gómez, Y ;
Rodríguez-Amo, JF ;
Santos-García, M ;
Sanz-Tejedor, MA .
TETRAHEDRON-ASYMMETRY, 2000, 11 (03) :789-796
[3]  
BOLTON PD, 1963, TETRAHEDRON LETT, P847
[4]  
BOOKERMILBURN KI, 1995, COMPREHENSIVE ORGANI, V2, P1039
[5]  
COREY EJ, 1972, TETRAHEDRON LETT, P3769
[6]  
Dunn P.J., 1995, COMPREHENSIVE ORGANI, V5, P741
[7]   NUCLEOPHILIC REACTIONS OF FLUOROOLEFINS [J].
ENGLAND, DC ;
MELBY, LR ;
DIETRICH, MA ;
LINDSEY, RV .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1960, 82 (19) :5116-5122
[8]   One-carbon homologation of carboxylic acids via BtCH2TMS:: A safe alternative to the Arndt-Eistert reaction [J].
Katritzky, AR ;
Zhang, SM ;
Hussein, AHM ;
Fang, YF ;
Steel, PJ .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (16) :5606-5612
[9]   Synthesis of 1-aryl-1,3-diyne and 2-aryl-1,1-dialkynylethene from the Sonogashira reactions of 2-aryl-1,1-dibromoethene [J].
Lee, HB ;
Huh, DH ;
Oh, JS ;
Min, GH ;
Kim, BH ;
Lee, DH ;
Hwang, JK ;
Kim, YG .
TETRAHEDRON, 2001, 57 (39) :8283-8290
[10]  
LEONARD J, 1995, ADV PRACTICAL ORGANI, P215