High-load, soluble oligomeric benzenesulfonyl azide: application to facile diazo-transfer reactions

被引:42
作者
Harned, AM
Sherrill, WM
Flynn, DL
Hanson, PR
机构
[1] Univ Kansas, Dept Chem, Lawrence, KS 66045 USA
[2] Univ Kansas, KU Ctr Excellence Chem Methodol & Lib Dev, Lawrence, KS 66047 USA
基金
美国国家卫生研究院; 美国国家科学基金会;
关键词
sulfonyl azide; ring-opening metathesis polymerization (ROMP); diazo transfer; high-load polymer; soluble polymer; supported reagents;
D O I
10.1016/j.tet.2005.08.120
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The development of a high-load, soluble oligomeric sulfonyl azide using ROM polymerization is reported. The utility in diazo transfer reactions with active methylene compounds is demonstrated using an efficient protocol, with most reactions showing completion in 30 min. The sulfonamide byproduct, being insoluble in the reaction solvent, can be completely removed by simple filtration through a silica gel SPE cartridge. (c) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码:12093 / 12099
页数:7
相关论文
共 61 条
[21]  
DURR H, 1981, Z NATURFORSCH B, V36, P1149
[22]  
Eames J, 2001, EUR J ORG CHEM, V2001, P1213
[23]  
Eymery F, 2000, SYNTHESIS-STUTTGART, P185
[24]   α-diazo carbonyl compounds:: An atractive estrategy in organic synthesis. [J].
Ferreira, VF ;
Pereira, LOR ;
de Souza, MCBV ;
Cunha, AC .
QUIMICA NOVA, 2001, 24 (04) :540-553
[25]  
Flynn DL, 2002, CURR OPIN DRUG DI DE, V5, P571
[26]  
FURNISS BS, 1989, VOGELS TXB PRACTICAL, P875
[27]   DIAZO TRANSFER-REACTION IN SOLID-STATE [J].
GHOSH, S ;
DATTA, I .
SYNTHETIC COMMUNICATIONS, 1991, 21 (02) :191-200
[28]   DIAZOETHENES - THEIR ATTEMPTED SYNTHESIS FROM ALDEHYDES AND AROMATIC KETONES BY WAY OF THE HORNER-EMMONS MODIFICATION OF THE WITTIG REACTION - A FACILE SYNTHESIS OF ALKYNES [J].
GILBERT, JC ;
WEERASOORIYA, U .
JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (10) :1837-1845
[29]   Organic synthesis on soluble polymer supports: Liquid-phase methodologies [J].
Gravert, DJ ;
Janda, KD .
CHEMICAL REVIEWS, 1997, 97 (02) :489-509
[30]   Polystyrene-supported benzenesulfonyl azide: A diazo transfer reagent that is both efficient and safe [J].
Green, GM ;
Peet, NP ;
Metz, WA .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (07) :2509-2511