A deprotonation pathway to reactive [B]CH2 boraalkenes.

ABSTRACT

The BH compounds IMes(ArF)BH(NTf2) (ArF C6F5 or FpXyl) were converted to the IMes(ArF)BCH2 boraalkenes in a three step reaction sequence of B-methylation with methyllithium, hydride abstraction and deprotonation. The BCH2 boraalkenes reacted with elemental sulfur to give a thiaborirane product. They underwent [2+2] cycloaddition reactions with carbon dioxide or sulfur dioxide to give four-membered boron containing heterocycles. The boraalkenes added strongly Lewis acidic boranes at their CH2 carbon atoms. The corresponding HB(C6F5)2/boraalkene adduct reduced carbon monoxide to a -OCH(C6F5)- moiety inside a five-membered heterocycle at the B-CH2-B template. The boraalkenes reacted with the [(Me2S)AuCl] reagent to form the corresponding (boraalkene)AuCl complexes.