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Abstract
1,3-Enynes containing allylic hydrogens cis to the alkyne are shown to act as one-carbon partners, rather than two-carbon partners, in various rhodium-catalyzed oxidative annulations. The mechanism of these unexpected transformations is proposed to occur through double C–H activation, involving a hitherto rare example of the 1,4-migration of a RhIII species. This phenomenon is general across a variety of substrates, and provides a diverse range of heterocyclic products.
Highlights
1,3-Enynes containing allylic hydrogens cis to the alkyne are shown to act as one-carbon partners, rather than two-carbon partners, in various rhodium-catalyzed oxidative annulations
This regioselectivity is maintained in the oxidative annulation of 1,3-enynes, as demonstrated by the groups of Fagnou (Scheme 1 a)[6a] and Ackermann,[6b] for example
We propose this reactivity arises from a hitherto rare example of 1,4-RhIII migration, which opens up new possibilities in CÀH functionalization reactions.[8]
Summary
1,3-Enynes containing allylic hydrogens cis to the alkyne are shown to act as one-carbon partners, rather than two-carbon partners, in various rhodium-catalyzed oxidative annulations. We propose this reactivity arises from a hitherto rare example of 1,4-RhIII migration, which opens up new possibilities in CÀH functionalization reactions.[8] This phenomenon is general for substrates containing directing groups such as enols, phenols, carboxylic acids, or imides, resulting in a range of heterocyclic products.
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