956014-23-6

Upstream product

• 930-68-7 cyclohexenone 
• 956014-22-5 (C₂H₄N₂(2,6-(iPr)2C₆H₃)2)BLi 
• 16853-85-3 lithium aluminium tetrahydride 
• 956014-21-4 2-bromo-1,3-bis[2,6-di-(propan-2-yl)phenyl]-1,3,2-diazaborolidine 
• 1333-74-0 hydrogen 
• 134030-22-1 N,N'-bis(2,6-diisopropylphenyl)ethane-1,2-diamine 

Relevant academic research and scientific papers

Boryl anion attacks transition-metal chlorides to form boryl complexes: Syntheses, spectroscopic, and structural studies on group 11 borylmetal complexes

(Chemical Equation Presented) Nucleophilic borylation: Transmetalation from boryllithium compounds to Group 11 transition-metal chlorides gives the corresponding boryl complexes (see scheme). Borylsilver and borylgold complexes that have three-center-two-

Assessing the bronsted basicity of diaminoboryl anions: Reactivity toward methylated benzenes and dihydrogen

Treatment of toluene or p-xylene with diaminoboryllithium results in consecutive reactions, involving boryl-anion-mediated deprotonation at the benzylic position followed by nucleophilic substitution at the boron center, producing benzylborane species and

Chemistry of boryllithium: Synthesis, structure, and reactivity

A series of lithium salts of boryl anion, boryllithiums, were synthesized and characterized by NMR spectroscopy and crystallographic analysis. In addition to the parent boryllithium compound 35a, structural modification of boryllithium, using saturated C-C and benzannulated C=C backbones in the five-membered ring and mesityl groups on the nitrogen atoms, also allowed generation of the corresponding boryllithium. The solid state structures of boryllithium showed that the boron-lithium bond is polarized where the boron atom is anionic in all (35a?DME)2, 35a?(THF)2, 35b?(THF)2, and 35c?(THF)2 when compared to the structures of hydroborane 38a-c and optimized free boryl anion opt-46a-c. Dissolution of the isolated single crystals of (35a?DME)2 and 35a?(THF)2 in THF-d8 showed that the boron-lithium bond remained in solution and free DME or THF molecules were observed. Temperature-dependent 11B NMR chemical shift changes of 35a were observed in THF-d8 or methylcyclohexane-d14, suggesting a change of chemical shift anisotropy around the boron center. The HOMO of opt-35a?(THF)2 had a lone pair character on the boron atom, as observed for phenyllithium, whereas the HOMO of hydroborane 38a corresponds to the π-orbital of the boron-containing five-membered heterocycle. The polarity of the B-Li bond, estimated by AIM analysis, was similar to that of alkyllithium. Boryllithiums 35a and 35b behave as a base or a boron nucleophile in reaction with organic electrophiles via deprotonation, SN2-type substitution, halogen-metal exchange or electron-transfer, 1,2-addition to a carbonyl group, and SNAr reaction. In the case of the reaction with CO2, intramolecular cyclization followed by CO elimination from borylcarboxylate anion and subsequent protonation gave hydroxyboranes 64a and 64b. The characters of the carbonyl groups in the borylcarbonyl compounds 60a, 60b, 61, 62, and 63a, which were obtained from the reaction of boryllithiums 35a and 35b, were investigated by X-ray crystallography, IR, and 13C NMR spectroscopy to show that the boryl substituent weakened the C=O bond when compared to carbon substituted analogues.

Syntheses, structures, and reactivities of borylcopper and -zinc compounds: 1,4-Silaboration of an α,β-unsaturated ketone to form a γ-siloxyallylborane

(Chemical Equation Presented) New borylcopper and borylzinc compounds were synthesized by transmetalation of boryllithium with metal halides. The 1,4-addition of lithium borylbromocuprate [BCu(μ2-Br)Li(thf) 3] to 2-cyclohexen-1-one as a boryl anion, followed by trapping of the resulting boron-substituted copper enolate with Me3SiCl, afforded the γ-siloxyallylborane.