Chemo-, Regio-, and Stereoselective cis-Hydroboration of 1,3-Enynes: Copper-Catalyzed Access to (Z,Z)- and (Z,E)-2-Boryl-1,3-dienes

Buchbinder, Nicklas W.Nguyen, Long H.Beck, Owen N.Bage, Andrew D.Slebodnick, CarlaSantos, Webster L.2025-11-072025-11-072024-07-171523-7060https://hdl.handle.net/10919/138902A copper-catalyzed alkyne-selective hydroboration of 1,3-enynes is disclosed, providing access to the previously elusive 2-boryl-1,3-dienes. Using CuOAc, Xantphos, and HBpin, Bpin was installed on the internal carbon of a series of symmetric and nonsymmetric 1,3-enynes, affording products with excellent Z:E selectivity. The utility of the 2-boryl-1,3-diene products was demonstrated by transformation to useful functional groups.application/pdfenCreative Commons Attribution 4.0 InternationalChemo-, Regio-, and Stereoselective cis-Hydroboration of 1,3-Enynes: Copper-Catalyzed Access to (Z,Z)- and (Z,E)-2-Boryl-1,3-dienesArticle - RefereedOrganic Lettershttps://doi.org/10.1021/acs.orglett.4c019292629390181301523-7052