An efficient synthesis of gem-diiodoolefins and (E)-iodoalkenes from propargylic amides with a Cu(i)/Cu(iii) cycle

文献情報

出版日 2015-03-27

DOI 10.1039/C5QO00043B

インパクトファクター 5.281

著者

Shuo Zhang, Ying Chen, Jianwu Wang, Yue Pan

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要旨

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.

掲載誌

Organic Chemistry Frontiers

CiteScore: 7.8

自己引用率: 8.7%

年間論文数: 724

Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry

An efficient synthesis of gem-diiodoolefins and (E)-iodoalkenes from propargylic amides with a Cu(i)/Cu(iii) cycle

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