9-Borabicyclo[3.3.1]nonane: a metal-free catalyst for the hydroboration of carbodiimides

Abstract

A 9-borabicyclo[3.3.1]nonane dimer is used as the first example of metal-free catalysts for the monohydroboration of carbodiimides with pinacol borane.

Organoaluminum Compounds as Catalysts for Monohydroboration of Carbodiimides

“…All these reactions resulted in the monohydroborated product even in the presence of 2 equivalents of HBpin (Scheme D) . Very recently, the commercially available hydroborane (H‐BBN) 2 was reported as a more efficient metal‐free catalyst for the monohydroboration of carbodiimides (Scheme E) …”

“…[16] Very recently, the commercially availableh ydroborane (H-BBN) 2 was reported as am ore efficient metal-free catalyst fort he monohydroboration of carbodiimides( Scheme 1E). [17] Herein, we report an unprecedented organoaluminum-catalyzed highly efficient and highly selective monohydroboration process of commercially available carbodiimide substrates with pinacolborane (HBpin) under mild and solvent-free reaction conditions. Five differenta luminum complexes (1-5)i ncluding aluminum hydride and aluminum alkyls were used to explore their catalytic properties (Scheme2).…”

Iron-catalysed hydroboration of non-activated imines and nitriles: kinetic and mechanistic studies

“…11 Hydroboration is an important transformation used to synthesize a wide variety of valuable products of industrial signicance such as commodity and ne chemicals, agrochemicals and materials. [12][13][14][15] Thus it is unsurprising that catalytic hydroboration of nitriles, [16][17][18][19][20] carbodiimides [21][22][23][24][25] and imines [26][27][28] are common methods used to prepare amines. Many experimental protocols have been studied; 29 catalysts employed in imine hydroboration range from main group elements, [30][31][32] preciousmetals [33][34][35][36] and, rare earth metals.…”

n‐Butyllithium Catalyzed Hydroboration of Nitriles and Carbodiimides

“…In the past period of time, the catalytic hydroboration of carbodiimide with HBpin has attracted more and more attention from the industry. However, only a few examples of the catalysis of main group metals have been confirmed [7c,10f,g,11,12] . As an extension of unsaturated compounds using n ‐BuLi as catalyst, we extended the scope of hydroboration to carbodiimides.…”