文献类型：期刊文献

英文题名：Regioselective nucleophilic addition of 3-aryl-5-difluoromethyl-isoxazoles to aldehydes

作者：Yang, Xueyan[1,2];Fang, Xiang[1,2];Zhang, Dong[1,2];Yu, Yanlin[1,2];Zhang, Zhengdong[1,2];Wu, Fanhong[1,2,3]

机构：[1]E China Univ Sci & Technol, Sch Chem & Mol Engn, Key Lab Adv Mat, Shanghai 200237, Peoples R China;[2]E China Univ Sci & Technol, Sch Chem & Mol Engn, Inst Fine Chem, Shanghai 200237, Peoples R China;[3]Shanghai Inst Technol, Sch Chem & Environm Engn, Shanghai 200235, Peoples R China

年份：2013

卷号：145

起止页码：1

外文期刊名：JOURNAL OF FLUORINE CHEMISTRY

收录：;WOS:【SCI-EXPANDED(收录号:WOS:000315252900001)，CCR-EXPANDED(收录号:WOS:000315252900001)】；

基金：The authors thank the National Natural Science Foundation of China (No. 20972050, No. 21172148 and No. 21202044) and the Science and Technology Commission of Shanghai Municipality (No. 10540501300) for financial support.

语种：英文

外文关键词：Difluoromethylation; Regioselectivity; Nucleophilic addition reaction; Isoxazole

摘要：A series of 5-difluoromethyl-isoxazoles 2 were prepared, and their regioselective nucleophilic addition to aldehydes was investigated. It was found that the nucleophilic difluoromethylation of aldehydes with 5-difluoromethyl-isoxazoles could be efficiently and uniquely achieved in the presence of LDA as a base that provides a large steric hindrance. In contrast, 3,4,5-trisubstituted 5-difluoromethyl isoxazoles were alternatively afforded as the sole product in moderate yields when n-BuLi was used as the base. (c) 2012 Elsevier B.V. All rights reserved.