TBAF-Mediated Reactions of 1,1-Dibromo-1-alkenes with Thiols and Amines and Regioselective Synthesis of 1,2-Heterodisubstituted Alkenes
作者:Hui Xu、Shaojin Gu、Wanzhi Chen、Dacheng Li、Jianmin Dou
DOI:10.1021/jo2000176
日期:2011.4.15
An efficient synthesis of trisubstituted alkenes including 1,2-heterodisubstituted alkenes has been described. Reactions of thiols and amines with 1,1-dibromo-1-alkenes in the presence of TBAF·3H2O afford (Z)-2-bromovinyl sulfides and (Z)-2-bromovinyl amines regio- and stereoselectively. The reaction proceeds under catalyst-free conditions with high efficiency. The coupling reactions of the obtained
已经描述了包括1,2-杂二取代烯烃的三取代烯烃的有效合成。在TBAF·3H 2 O存在下,硫醇和胺与1,1-二溴-1-烯的反应在区域和立体上提供(Z)-2-溴乙烯基硫化物和(Z)-2-溴乙烯基胺。该反应在无催化剂的条件下高效地进行。所获得的带有溴原子的产物与苯乙炔和苯基硼酸的偶联反应以良好或优异的收率得到三取代的烯烃。与各种N,O,S和P亲核试剂的交叉偶联选择性地生成1,2-N,O,1,2-N,S,1,2-S,P,1,2-S,S和1 ,2-S,O杂二取代的烯烃。