标题:An efficient synthesis of gem-diiodoolefins and (E)-iodoalkenes from propargylic amides with a Cu(I)/Cu(III) cycle
作者:Shuo Zhang;Ying Chen;Jianwu Wang
作者机构:Key Lab for Colloid and Interface Chemistry of Education Ministry, School of chemistry and Chemical Engineering, Shandong Univer
来源:Organic Chemistry Frontiers
出版年:2015
期:5
页码:578-585
摘要:gem-Dihaloalkenes are very important building blocks widely used in organic synthesis. However, the synthetic methods available for this functional group are very limited. Starting from an unexpected copper-catalyzed cyclization of propargylic amides, a new route for the synthesis of gem-dihaloalkenes was developed. According to the plausible Cu(I)/Cu(III) catalytic cycle, another oxidative iodination protocol was developed. Through this improved method, a series of gem-diiodoolefins were synthesized in high yields. In addition, (E)-iodoalkenes could also be synthesized efficiently using the same approach, which is complementary to the gold-catalyzed reaction giving (Z)-iodoalkenes. These iodoolefins could be further transformed into various trisubstituted or tetrasubstituted alkenes, enynes, dienes and trienes with palladium-catalyzed coupling reactions.
资源类型:期刊论文
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