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- Title
Transition Metal‐Free Regio‐ and Stereo‐Selective trans Hydroboration of 1,3‐Diynes: A Phosphine‐Catalyzed Access to (E)‐1‐Boryl‐1,3‐Enynes.
- Authors
Jos, Swetha; Szwetkowski, Connor; Slebodnick, Carla; Ricker, Robert; Chan, Ka Lok; Chan, Wing Chun; Radius, Udo; Lin, Zhenyang; Marder, Todd B.; Santos, Webster L.
- Abstract
We report a transition metal‐free, regio‐ and stereo‐selective, phosphine‐catalyzed method for the trans hydroboration of 1,3‐diynes with pinacolborane that affords (E)‐1‐boryl‐1,3‐enynes. The reaction proceeds with excellent selectivity for boron addition to the external carbon of the 1,3‐diyne framework as unambiguously established by NMR and X‐ray crystallographic studies. The reaction displays a broad substrate scope including unsymmetrical diynes to generate products in high yield (up to 95 %). Experimental and theoretical studies suggest that phosphine attack on the alkyne is a key process in the catalytic cycle.
- Subjects
HYDROBORATION; PHOSPHINE; X-rays; BORON; STEREOSELECTIVE reactions
- Publication
Chemistry - A European Journal, 2022, Vol 28, Issue 63, p1
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.202202349