Boron Reagents in Process Chemistry:  Excellent Tools for Selective Reductions

Experimental and Theoretical Studies of the Potential Interconversion of the Amine–Borane iPr2NH·BH(C6F5)2 and the Aminoborane iPr2N=B(C6F5)2 Involving Hydrogen Loss and Uptake

“…Adjacent molecules within the unit cell were in close proximity to one another, as exemplified by the intermolecular C(10)···F(2) separation of 3.231 Å, and the atom connectivity within each molecule confirmed the formulation based on spectroscopic methods. The angles around B (1) and N(1) summed to 438 and 448°, respectively, which were consistent with the expected tetrahedral geometries at each centre. The B(1)-N(1) bond length of 1.628(3) Å falls within the range observed for both tertiary aminesecondary borane adducts [1.578 (8) [61][62][63][64] and is therefore unremarkable.…”

“…[1][2][3] Of these species, amine-borane adducts, R x NH 3-x ·BH 3 , are an interesting subclass that can exhibit unique reactivity due to the presence of both protic and hydridic hydrogen atoms. The elimination of dihydrogen from molecules of this type affords new intra-or intermolecular boron-nitrogen bonds, and a wide range of catalysts have now been reported which can promote such processes under mild conditions (Scheme 1).…”

Recent Advances in Azaborine Chemistry

“…Today, boron-containing compounds represent a powerful tool for synthetic chemists. [4–7] In most targeted synthetic applications, however, the element boron typically is not part of the final functional structure. Because of boron's unique electronic structure and its ability to form covalent bonds with carbon, the inclusion of boron in organic structures has recently received significant attention in biomedical research [8] and in optoelectronic materials applications.…”

Reductions of aldehydes and ketones with a readily available N-heterocyclic carbene borane and acetic acid

“…Among the numerous hydride reagents available for such reductions, boron reductants are widely used in the field of synthetic chemistry due to their availability and favorable reaction profiles [1–3]. For instance, sodium borohydride (NaBH 4 ) is an inexpensive salt that is one of the most popular hydride sources for the reduction of aldehydes and ketones [4].…”