143122-91-2

Upstream product

• 21205-91-4 9-borabicyclo[3.3.1]nonane dimer 
• 100-47-0 benzonitrile 
• 280-64-8 9-bora-bicyclo[3.3.1]nonane 

Downstream Products

• 538-51-2 benzylidene phenylamine 
• 143122-97-8 9-(benzylideneamino)-9-borabicyclo{3.3.1}nonane(C₈H₁₄BH) 

Relevant academic research and scientific papers

Double and Single Hydroboration of Nitriles Catalyzed by a Ruthenium-Bis(silyl)xanthene Complex: Application to One-Pot Synthesis of Diarylamines and N-Arylimines

A ruthenium complex bearing a bis(silyl)xanthene chelate ligand xantsil, i.e. Ru[κ3(Si,O,Si)-xantsil](CO)(PCyp3) (1a, Cyp = cyclopentyl), was found to catalyze both double and single hydroboration reactions of nitriles with pinacolborane (HBpin) and 9-borabicyclo[3.3.1]nonane (9-BBN) to give bis(boryl)amines 2 and N-borylimines 3, respectively, in mostly >99% yields. By combination of these reactions with subsequent palladium-catalyzed deborylative C-N coupling reactions of 2 and 3 with a 1:1 mixture of bromoarenes and KOtBu, one-pot synthetic routes to tertiary N,N-diarylamines 4 and N-arylaldimines 5 from nitriles were developed.

Monomeric Aldimino-diorganoboranes and Aspects of Their Chemistry

The hydroboration of benzo-, tolu-, p-methoxybenzo-, or pivalonitriles with bis(9-borabicyclononane) (9H-9-BBN)2 affords the corresponding 9-aldimino-9-borabicyclononanes (1a-d) in about 80percent yields.Compounds 1a and 1d readily react with an excess of (9H-9-BBN)2 to form the 1:1 adducts 2a or 2d, respectively, containing a NB2H four-membered ring (X-ray structure of 2a).The adducts 2 are thermally rather stable.Compound 2a is converted to benzylbis(1,5-cyclooctanediylboryl)amine (3a) only after 48 h at reflux in mesitylene.Compounds 1a-d are stable towards strong N-bases.Compound 1d reacts with Et2O*BF3 to form 9-fluoro-9-borabicyclononane (4) and the 1:1 cyclic adduct (5d) of (2,2-dimethylpropylideneamino)difluoroborane (6d) and 1d.Key Words: Nitriles / Hydroboration / Bis(9H-9-borabicyclononane) / N-Base-Organoboron adducts