Three-component regioselective carboamidation of 1,3-enynes via rhodium(iii)-catalyzed C-H activation

Rhodium-catalyzed regio- and stereoselective three-component carboamidation of 1,3-enynes has been realized using indoles and dioxazolones as the functionalizing reagents. A wide range of multi-substituted skipped 1,4-dienes have been constructed in good yields and excellent stereoselectivity. The stereoselectivity is under substrate control. 1,3-Enynes bearing a relatively bulky alkyne terminus reacted with Z-selectivity. In contrast, a sterically less hindered alkyne terminus tends to predominantly give the E-configured skipped diene.

Automated summary

In this study, a rhodium-catalyzed regio- and stereoselective three-component carboamidation of 1,3-enynes was achieved using indoles and dioxazolones as functionalizing reagents. A wide range of multi-substituted skipped 1,4-dienes were synthesized in good yields and excellent stereoselectivity. The stereoselectivity is determined by the substrate, with bulky alkyne terminus favoring Z-selectivity and less hindered alkyne terminus predominantly giving the E-configured skipped diene.