1566593-63-2

Upstream product

• 434-45-7 2,2,2-Trifluoroacetophenone 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 1594137-74-2 [Rh{η³-C(CF3)(OB(pinacolato))C6H5}(PEt3)2] 
• 73183-34-3 bis(pinacol)diborane 

Downstream Products

• 340-04-5 1-phenyl-2,2,2-trifluoromethylethanol 

Relevant academic research and scientific papers

Metal-free σ-bond metathesis in 1,3,2-diazaphospholene-catalyzed hydroboration of carbonyl compounds

The first metal-free catalytic hydroboration of carbonyl derivatives has been developed in which a catalytic amount of 1,3,2-diazaphospholene effectively promotes a hydroboration reaction of aliphatic and aromatic aldehydes and ketones. The reaction mecha

Formation of a hydride containing amido-zincate using pinacolborane

Amido-zincates containing hydrides are underexplored yet potentially useful complexes. Attempts to access this type of zincate through combining amido-organo zincates and pinacolborane (HBPin)viaZn-C/H-BPin exchange led instead to preferential formation of amide-BPin and/or [amide-BPin(Y)]?(Y = Ph, amide, H), when the amide is hexamethyldisilazide or 2,2,6,6-tetramethylpiperidide and the hydrocarbyl group was phenyl or ethyl. In contrast, the use of a dipyridylamide (dpa) based arylzinc complex led to Zn-C/H-BPin metathesis being the major outcome. Independent synthesis and full characterisation of two LnLi[(dpa)ZnPh2] (L = THF,n= 3; L = PMDETA,n= 1) complexes,1and3, respectively, enabled reactivity studies that demonstrated that these species display zincate type reactivity (by comparison to the lower reactivity of the neutral complex (Me-dpa)ZnPh2,4, Me-dpa = 2,2′-dipyridyl-N-methylamine). This included1performing the rapid deprotonation of 4-ethynyltoluene and also phenyl transfer to α,α,α-trifluoroacetophenone in contrast to neutral complex4. Complex1reacted with one equivalent of HBPin to give predominantly PhBPin (ca.90%) and a lithium amidophenylzincate containing a hydride unit, complex7-A, as the major zinc containing product. Complex7-Atransfers hydride to an electrophile preferentially over phenyl, indicating it reacts as a hydridozincate. Attempts to react1with >1 equivalent of HBPin or with catecholborane led to more complex outcomes, which included significant borane and dpaZn substituent scrambling, two examples of which were crystallographically characterised. While this work provides proof of principle for Zn-C/H-BPin exchange as a route to form an amido-zincate containing a hydride, amido-organozincates that undergo more selective Zn-C/H-BPin exchange still are required.

Synthesis and Structure of a Dimeric Yttrium Complex [LSi(BH3)(C5Me4)Y(CH2SiMe3)2]2(L = PhC(N tBu)2) and Its Catalytic Application for Hydroboration of Ketones and Aldehydes

Treatment of cyclopentadienyl-amidinate silylene LSi(C5HMe4) (L = PhC(NtBu)2, 1) with BH3·THF yielded the silylene-borane-functionalized tetramethylcyclopentadiene LSi(BH3)-(C5HMe4) (2), which reacted with Y(CH2SiMe3)3(THF)2 to give the dimeric yittrium complex [LSi(BH3)-(C5Me4)Y(CH2SiMe3)2]2 (3). X-ray structural analysis disclosed that the dimeric structure was formed through the BH3 bridging to the yttrium atom. Complex 3 enabled catalytic hydroboration of ketones and aldehydes with excellent efficiency and chemoselectivity.

An Unsymmetric Imino-Phosphanamidinate Ligand and its Y(III) Complex: Synthesis, Characterization, and Catalytic Hydroboration of Carbonyl Compounds

An imino-phosphanamide ligand, [NHIiPr2Me2P(Ph)NH-2,6-iPr2C6H3] (LH), containing two different N-substituents was prepared by the direct reaction of the lithium salt of N-heterocyclic imine (NHI) with phenylchloro-2,6-diisopropylphenyl phosphanamine, PhP(

[(Me6TREN)MgOCHPh2][B(C6F5)4]: A Model Complex to Explore the Catalytic Activity of Magnesium Alkoxides in Ketone Hydroboration

The sterically hindered monomeric alkoxomagnesium compound [(Me6TREN)MgOCHPh2][B(C6F5)4] (1) has been used to explore the role of magnesium alkoxides in ketone hydroboration. Experiments and DFT calcu

Hydroboration of carbonyls and imines by an iminophosphonamido tin(ii) precatalyst

A novel three-coordinated tin(ii) chloride [Ph2P(NtBu)2]SnCl (1) supported by an N,N′-di-tert-butyliminophosphonamide having two phenyl groups on the phosphorus atom was synthesized by the reaction of the starting lithium iminophosphonamide [Ph2P(NtBu)2]L

Structural Elucidation of Silver(I) Amides and Their Application as Catalysts in the Hydrosilylation and Hydroboration of Carbonyls

This study details the isolation and characterisation of three novel silver(I) amides in solution and solid-state, [Ag(Cy3P)(HMDS)] 2, [Ag(Cy3P){N(TMS)(Dipp)}] 3 and [Ag(Cy3P)2(NPh2)] 4. Their catalytic abilities have proved successful in hydroboration and hydrosilylation reactions with a full investigation performed with complex 2. Both protocols proceed under mild conditions, displaying exceptional functional-group tolerance and chemoselectivity, in excellent conversions at competitive reaction times. This work reveals the first catalytic hydroboration of aldehydes and ketones performed by a silver(I) catalyst.

Potassium Fluoride-Catalyzed Hydroboration of Aldehydes and Ketones: Facile Reduction to Primary and Secondary Alcohols

A catalytic hydroboration of various ketones and aldehydes can be achieved in the presence of inexpensive and commercially available inorganic salts containing fluoride anion. As a result, the reduction of carbonyl moieties to the corresponding primary and secondary alcohols can be achieved at room temperature under mild conditions.

Hydroboration of Aldehydes, Ketones, and Carbodiimides Promoted by Mono(imidazolin-2-iminato) Hafnium Complexes

Imidazolin-2-iminato hafnium complexes of the type [(ImRN)Hf(CH2Ph)3] were synthesized (ImtBuN = 1,3-di-tert-butylimidazolin-2-iminato); ImDippN = 1,3-bis(2,6-diisopropylphenyl)-imidazolin-2-iminato.

Space Craft-like Octanuclear Co(II)-Silsesquioxane Nanocages: Synthesis, Structure, Magnetic Properties, Solution Behavior, and Catalytic Activity for Hydroboration of Ketones

Two novel space craft-like octanuclear Co(II)-silsesquioxane nanocages, {Co8[(MeSiO2)4]2(dmpz)8} (SD/Co8a) and {Co8[(PhSiO2)4]2(dmpz)8} (SD/Co8b)