TY  - JOUR
A1  - Jos, Swetha
A1  - Szwetkowski, Connor
A1  - Slebodnick, Carla
A1  - Ricker, Robert
A1  - Chan, Ka Lok
A1  - Chan, Wing Chun
A1  - Radius, Udo
A1  - Lin, Zhenyang
A1  - Marder, Todd B.
A1  - Santos, Webster L.
T1  - Transition Metal‐Free Regio‐ and Stereo‐Selective trans Hydroboration of 1,3‐Diynes: A Phosphine‐Catalyzed Access to (E)‐1‐Boryl‐1,3‐Enynes
JF  - Chemistry – A European Journal
N2  - 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.
KW  - enediyne
KW  - enyne
KW  - hydroboration
KW  - organocatalytic
KW  - stereoselective
Y1  - 2022
U6  - http://nbn-resolving.de/urn/resolver.pl?urn:nbn:de:bvb:20-opus-293784
VL  - 28
IS  - 63
ER  -