Abstract
A novel multicomponent coupling reaction involving the iridium-catalyzed 1,5-difunctionalization of 1,3-enynes with arylboronic acids and triazinanes is described. A key step in this 1,5-(aryl)aminomethylation reaction is the alkenyl-to-allyl 1,4-iridium(i) migration.
Highlights
A novel multicomponent coupling reaction involving the iridium-catalyzed 1,5-difunctionalization of 1,3-enynes with arylboronic acids and triazinanes is described
We report the first example of an iridium-catalyzed multicomponent coupling between 1,3-enynes, arylboronic acids, and triazinanes that results in a novel 1,5functionalization to give 1,3-dienes
The key step in this reaction involves an alkenyl-to-allyl 1,4-iridium(I) migration that enables the functionalization of an otherwise unreactive C-H bond. This overall 1,5-(aryl)aminomethylation[6] reaction introduces nitrogen functionality with the concomitant formation of two new carbon–carbon bonds, complementing more well-known hydroaminomethylation and hydroamidomethylation reactions that result in only one new carbon–carbon bond.[7,8]
Summary
A novel multicomponent coupling reaction involving the iridium-catalyzed 1,5-difunctionalization of 1,3-enynes with arylboronic acids and triazinanes is described. We report the first example of an iridium-catalyzed multicomponent coupling between 1,3-enynes, arylboronic acids, and triazinanes that results in a novel 1,5functionalization to give 1,3-dienes.
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