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. Author manuscript; available in PMC: 2018 Mar 15.
Published in final edited form as: J Am Chem Soc. 2017 Mar 1;139(10):3868–3875. doi: 10.1021/jacs.7b00445

Scheme 5. Stereoselective Cobalt-Catalyzed 1,1-Diboration of Terminal Alkynes with PinB−BDana.

Scheme 5

aReagents and conditions: alkyne 2 (0.50 mmol), PinB–BDan (0.50 mmol), 1 (5 mol %), THF, 50 °C, 36 h. Numbers in parentheses are yields of isolated products obtained after purification by flash chromatography on silica gel. Thermal ellipsoids in ORTEP diagram at 50% probability; hydrogen atoms except vinyl C–H omitted for clarity. Olefin geometry of products 6a, 6d, 6e, and 6g assigned by analogy to the solid-state structure.