Transformation of Aldehydes into (E)-1-Alkenylsilanes and (E)-1-Alkenylboronic Esters with a Catalytic Amount of a Chromium Salt

Abstract (Diiodomethyl)trimethylsilane (Me3SiCHI2, 1) is produced by treatment of iodoform with manganese in the presence of Me3SiCl. Aldehydes are converted to (E)-1-trimethylsilyl-1-alkenes in a stereoselective manner with a geminal dichromium reagent generated from 1, manganese, Me3SiCl, and a catalytic amount of CrCl3[thf]3 in THF. Similarly, (E)-1-alkenylboronic esters are prepared stereoselectively in good to excellent yields by treatment of aldehydes with a geminal dichromium reagent derived from Cl2CHB(OR)2 [(OR)2 = OCMe2CMe2O] and LiI instead of 1.