Stereoselective synthesis of (Z)-β-arylvinyl bromides from anti-2,3-dibromo-3-arylpropanoic acids

被引:1
作者
Xv, Wenjing [1 ]
Zhang, Wensheng [1 ]
Zhang, Fei [2 ]
Kuang, Chunxiang [3 ]
机构
[1] Jiaozuo Teachers Coll, Sch Sci, Jiaozuo 450001, Peoples R China
[2] Jiaozuo Vocat Educ Ctr, Jiaozuo 454001, Peoples R China
[3] Tongji Univ, Dept Chem, Shanghai 200092, Peoples R China
基金
中国国家自然科学基金;
关键词
stereoselective synthesis; (Z)-beta-arylvinyl bromide; decarboxylation; NaN3; ONE-POT SYNTHESIS; MICROWAVE-INDUCED REACTION; CROSS-COUPLING REACTIONS; STEREOSPECIFIC SYNTHESIS; VINYLIC ORGANOBORANES; ALKENYL HALIDES; CONVENIENT; (Z)-1-BROMO-1-ALKENES; (Z)-1-HALO-1-ALKENES; VINYLSILANES;
D O I
10.3184/174751914X13896335381533
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A novel method for the stereoselective synthesis of (Z)-beta-arylvinyl bromides in excellent yields by debrominative decarboxylation of anti-2,3-dibromo-3-arylpropanoic acids using NaN3 was developed. This facile transformation was achieved under room temperature for 1-2 h.
引用
收藏
页码:115 / 117
页数:3
相关论文
共 30 条
[1]   VINYLIC ORGANOBORANES .13. A CONVENIENT STEREOSPECIFIC SYNTHESIS OF (Z)-1-HALO-1-ALKENES FROM 1-ALKYNES VIA (E)-1-ALKENYLBORANE DERIVATIVES WITH HALOGENS [J].
BROWN, HC ;
SUBRAHMANYAM, C ;
HAMAOKA, T ;
RAVINDRAN, N ;
BOWMAN, DH ;
MISUMI, S ;
UNNI, MK ;
SOMAYAJI, V ;
BHAT, NG .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (26) :6068-6075
[2]   VINYLIC ORGANOBORANES .12. SYNTHESIS OF (Z)-1-HALO-1-ALKENES VIA HYDROBORATION OF 1-HALO-1-ALKYNES FOLLOWED BY PROTONOLYSIS [J].
BROWN, HC ;
BLUE, CD ;
NELSON, DJ ;
BHAT, NG .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (26) :6064-6067
[3]   MECHANISMS OF ELIMINATION REACTIONS .2. THE SPONTANEOUS DECOMPOSITION OF SALTS OF BETA-HALO ACIDS .2. TRANS-CINNAMIC ACID DIBROMIDE [J].
CRISTOL, SJ ;
NORRIS, WP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1953, 75 (11) :2645-2646
[4]   The mechanisms of the Stille reaction [J].
Espinet, P ;
Echavarren, AM .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (36) :4704-4734
[5]  
Grovenstein J. E., 1953, J AM CHEM SOC, V75, P2639
[6]   Copper-catalyzed coupling of amides and carbamates with vinyl halides [J].
Jiang, L ;
Job, GE ;
Klapars, A ;
Buchwald, SL .
ORGANIC LETTERS, 2003, 5 (20) :3667-3669
[7]   Novel One-Pot Synthesis of Functionalized (Z)-2-Arylvinyl Bromides [J].
Jiang, Yubo ;
Kuang, Chunxiang .
SYNTHETIC COMMUNICATIONS, 2009, 39 (23) :4298-4308
[8]   A mild procedure for the stereospecific transformation of trans cinnamic acid derivatives to cis β-bromostyrenes [J].
Kim, SH ;
Wei, HX ;
Willis, S ;
Li, GG .
SYNTHETIC COMMUNICATIONS, 1999, 29 (23) :4179-4185
[9]   Synthesis of (Z)-1-bromo-1-alkenes and terminal alkynes from anti-2,3-dibromoalkanoic acids by microwave-induced reaction [J].
Kuang, CX ;
Yang, Q ;
Senboku, H ;
Tokuda, M .
TETRAHEDRON, 2005, 61 (16) :4043-4052
[10]   Convenient and stereoselective synthesis of (Z)-1-bromo-1-alkenes by microwave-induced reaction [J].
Kuang, CX ;
Senboku, H ;
Tokuda, M .
TETRAHEDRON LETTERS, 2001, 42 (23) :3893-3896