1353044-15-1

Upstream product

• 104-87-0 4-methyl-benzaldehyde 
• 185990-03-8 dimethylphenyl(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)silane 
• 768-33-2 phenyldimethylsilyl chloride 

Downstream Products

• 1504663-23-3 [dimethylphenylsilyl(p-tolyl)methoxy]trimethylsilane 
• 18584-20-8 4-methylmandelic acid 
• 13305-13-0 methyl (+/-)-α-hydroxy-α-(4-methylphenyl)acetate 

Relevant academic research and scientific papers

Complexes (ER3 = SiMe2Ph, SiPh3, SnMe3): From Linear, Mononuclear Complexes to Polynuclear Complexes with Ultrashort CuI···CuI Distances

A series of complexes of the type [(NHC)Cu-ER3] (NHC = IDipp, IMes, ItBu, Me2IMe, and ER3 = SiMe2Ph, SiPh3, SnMe3) and [(NHC)Cu-R′] (NHC = IDipp, Me2IMe and R′ = Ph, C - CPh) was synthesized in good yields by the reaction of the corresponding [(NHC)Cu-OtBu] complex with the respective silylborane pinB-ER3 (pin = OCMe2CMe2O; ER3 = SiMe2Ph, SiPh3), the stannylborane ((C2H4)(iPrN)2)B-SnMe3, or a boronic acid ester pinB-R′ (R′ = Ph, C - CPh). Solid structures of all complexes were systematically studied by X-ray diffraction analysis. The solid state structures of the complexes [(NHC)Cu-ER3] show a dependence of the structural motif from the steric properties of the NHC ligand. The sterically demanding NHC ligands (IDipp, IMes, ItBu) lead to monomeric, linear complexes [(NHC)Cu-ER3], while with the less demanding Me2IMe ligand, polynuclear, μ-ER3-bridged complexes with ultrashort Cu···Cu distances are observed. For the related complexes [(NHC)Cu-R′] no analogous complexes with bridging anionic ligands are realized. Instead, irrespective of the NHC ligand, linear coordinated copper complexes of different types are formed. 29Si heteronuclear solution NMR spectroscopic data on [(NHC)CuI-SiR3] exhibit distinctly different chemical shifts for the (in the solid state) monomeric and dimeric complexes suggesting different structure types also in solution. This agrees well with the observation of a trinuclear complex [(Me2IMe)Cu-SnMe3]3 both in the solid state and in solution. Initial catalytic studies suggest that [(NHC)Cu-OtBu] complexes (NHC = ItBu, Me2IMe) are, in addition to the established [(IDipp)Cu-OtBu] complex, efficient precatalysts for the silylation of aldehydes and α,β-unsaturated ketones with pinB-SiMe2Ph.

[(18-C-6)K][(NC)CuI-SiMe2Ph], a Potassium Silylcyanocuprate as a Catalyst Model for Silylation Reactions with Silylboranes: Syntheses, Structures, and Catalytic Properties

CuI-catalyzed silylation reactions involving silylboranes (in particular, pinB-SiMe2Ph (1)) as silyl sources have recently gained considerable attention. One of the most efficient and versatile and yet simplest catalyst systems consi

Carboxylation with CO2 via brook rearrangement: Preparation of α-hydroxy acid derivatives

In the presence of CsF, a wide range of α-substituted α-siloxy silanes were carboxylated under a CO2 atmosphere (1 atm) via Brook rearrangement. A variety of α-substituents including aryl, alkenyl, and alkyl groups were tolerated to afford α-hydroxy acids in moderate-to-high yields. One-pot synthesis from aldehydes using PhMe2SiLi and CO 2 was also possible, providing α-hydroxy acids without the isolation of an α-hydroxy silane.

Copper-catalyzed 1,2-addition of nucleophilic silicon to aldehydes: Mechanistic insight and catalytic systems

Activation of the Si-B inter-element bond with copper(I) alkoxides produces copper-based silicon nucleophiles that react readily with aldehydes to yield α-silyl alcohols (that is, α-hydroxysilanes) after hydrolysis. Two independent protocols were develope