120789-33-5

Upstream product

• 21205-91-4 9-borabicyclo[3.3.1]nonane dimer 
• 3768-55-6 N-trimethylsilylaniline 
• 116951-81-6 bis(1,5-cyclooctanediylboryl)monoselenide 
• 62-53-3 aniline 
• 120789-32-4 bis(1,5-cyclooctanediylboryl)diselenide 
• 280-64-8 9-bora-bicyclo[3.3.1]nonane 

Relevant academic research and scientific papers

Reaction of 9-borabicyclo[3.3.1]nonane with N-trimethylsilylamines - Cleavage of the N-Si or N-H bond

The reaction of dimeric 9-borabicyclo[3.3.1]nonane 1 with N-trimethylsilyl-aniline 2 affords 9-anilino-9-borabicyclo[3.3.1]nonane 5 by elimination of trimethylsilane. In contrast, 1 reacts with the N-trimethylsilyl-2-aminopyridines 3 and 4 selectively by

Alkaline-Earth-Catalyzed Dehydrocoupling of Amines and Boranes

Dehydrocoupling reactions between the boranes HBpin and 9-borabicyclo[3.3.1]nonane and a range of amines and anilines ensue under very mild reaction conditions in the presence of a simple β-diketiminato magnesium n-butyl precatalyst. The facility of the reactions is suggested to be a function of the Lewis acidity of the borane substrate, and is dictated by resultant pre-equilibria between, and the relative stability of, magnesium hydride and borohydride intermediates during the course of the catalysis.

Mesoionic N-heterocyclic olefin catalysed reductive functionalization of CO2for consecutiveN-methylation of amines

A mesoionic N-heterocyclic olefin (mNHO) was introduced as a metal-free catalyst for the reductive functionalization of CO2leading to consecutive doubleN-methylation of primary amines in the presence of 9-borabicyclo[3.3.1]nonane (9-BBN). A wide range of secondary amines and primary amines were successfully methylated under mild conditions. The catalyst sustained over six successive cycles ofN-methylation of secondary amines without compromising its activity, which encouraged us to check its efficacy towards doubleN-methylation of primary amines. Moreover, this method was utilized for the synthesis of two commercially available drug molecules. A detailed mechanistic cycle was proposed by performing a series of control reactions along with the successful characterisation of active catalytic intermediates either by single-crystal X-ray study or by NMR spectroscopic studies in association with DFT calculations.

An Aluminum Dihydride Working as a Catalyst in Hydroboration and Dehydrocoupling

The well-defined aluminum dihydride LAlH2 (L = HC(CMeNAr)2, Ar = 2,6-Et2C6H3) (1) operates in catalysis like a transition metal complex. The catalytic activity of 1 for hydroboration of terminal alkynes was investigated. Furthermore, catalyst 1 effectively initiated the dehydrocoupling of boranes with amines, thiols, and phenols, respectively, to form compounds with B-E bonds (E = N, S, O) under elimination of H2. Quantum mechanical calculations indicate that hydroboration and dehydrocoupling reactions occur via three consecutive cycloaddition reactions involving the activation of the X-H (X = Al, B, C, and O) σ-bonds.

Catalyst-free dehydrocoupling of amines, alcohols, and thiols with pinacol borane and 9-borabicyclononane (9-BBN)

Contrary to recent reports, the dehydrocoupling of pinacol borane and 9-borabicyclononane with a variety of amines, alcohols and thiols can be achieved under mild conditions without catalyst. This process involves the formation of Lewis acid-base adducts

1,5-Cyclooctanediylboryl Selenides - Preparation, Characterisation, and Application

Bis(1,5-cyclooctanediylboryl) selenide (C8H14B)2Se (1) is obtained quantitatively from bis(9-borabicyclononane) (9-BBN)2 and elemental selenium in mesitylene at 150 deg C accompanied by evolution of hydrogen.Bis(1,5-cyclooctanediylboryl) diselenide (C8H14BSe)2 (2) is prepared efficiently from 1 with selenium in mesitylene at 120 deg C. 9-(Hydroseleno)-9-BBN (1H) together with 9-(phenylamino)-9-BBN (3) is easily obtained from 1 and aniline. - γ-Picoline (γPic) reacts with 1 to give the 2:1 addition compound γPic2-1, trimethylphosphane (TMP) with 1 forms the 1:1 addition compound TMP-1.Selenide 1 reacts spontaneously at room temperature with trialkoxyboranes B(OR)3 or with ClnAl(C2H5)3-n compounds exchanging the substituents. - The 1:1 addition compounds γPic-1H, TMP-1H, and Q-1H, are prepared from 1H with γPic, TMP, and quinuclidin (Q), respectively. - 1, 1H, and 2 undergo Se/O exchange reactions with organic and other oxygenated compounds and add to certain CC triple bonds.Pure Fe2Se3 is prepared quantitatively from 1 and Fe2O3. - Key Words: Boryl selenides, 1,5-cyclooctanediyl- / 9-Borabicyclononane, 9-hydroseleno- / Selenidation reagents / Lewis base - organoboron selenium compounds / Borane exchange reactions