Face to face activation of phenylselenium boranes with ¿

Identifier:  PC:2633

Handle: https://hdl.handle.net/20.500.11797/PC2633

Authors:  Sanz, X.; Vogels, C.M.; Decken, A.; Bo, C.; Westcott, S.A.; Fernández, E.

Abstract:
Activated olefins directly react with phenylselenium boranes, at room temperature, without the need of metal or organocatalytic assistance. A simple mechanism that involves the interaction of the electron pair of carbonyl functional group in ¿,¿-unsaturated ketones and aldehydes, with the empty p orbital of the boron atom, justifies the efficient reaction towards the kinetically and thermodynamically most stable 1,4-addition product. Up to 12 examples of ¿ (phenylseleno) substituted ketones and aldehydes have been prepared with moderate to high yield. The simplicity and efficiency of this new reactivity generates new strategic platforms towards the C-Se bond formation and opens non existing pathways to create C-heteroatom bonds, as a general tool