Issue 5, 2015

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

Abstract

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.

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

Supplementary files

Article information

Article type
Research Article
Submitted
04 Feb 2015
Accepted
26 Mar 2015
First published
27 Mar 2015

Org. Chem. Front., 2015,2, 578-585

Author version available

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

S. Zhang, Y. Chen, J. Wang, Y. Pan, Z. Xu and C. Tung, Org. Chem. Front., 2015, 2, 578 DOI: 10.1039/C5QO00043B

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