Face to face activation of phenylselenium boranes with α,β-unsaturated carbonyl substrates: facile synthesis of C-Se bonds

author can archive pre-print (ie pre-refereeing). 12 meses de embargo DOI: 10.1039/c4cc02098g URL: http://pubs.rsc.org/en/Content/ArticleLanding/2014/CC/c4cc02098g#!divAbstract Filiació URV: SI 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