18080-99-4

Upstream product

• 98-13-5 Phenyltrichlorosilane 
• 13139-86-1 4-methoxyphenyl magnesium bromide 
• 694-53-1 phenylsilane 
• 696-64-0 (4-methoxy-phenyl)-silane 
• 696-62-8 para-iodoanisole 

Downstream Products

• 102158-66-7 (4-methoxy-phenyl)-phenyl-o-tolyl-silane 
• 18056-34-3 (4-methoxyphenyl)(phenyl)silanediol 
• 18834-15-6 (4-methoxy-phenyl)-(4-phenoxy-phenyl)-phenyl-p-tolyl-silane 
• 18849-19-9 (4-methoxy-phenyl)-methyl-(4-phenoxy-phenyl)-phenyl-silane 

Relevant academic research and scientific papers

Divalent Ytterbium Complex-Catalyzed Homo- and Cross-Coupling of Primary Arylsilanes

Redistribution of primary silanes through C-Si and Si-H bond cleavage and reformation provides a straightforward synthesis of secondary silanes, but the poor selectivity and low efficiency severely hinders the application of this synthetic protocol. Here, we show that a newly synthesized divalent ytterbium alkyl complex exhibits unprecedentedly high catalytic activity toward the selective redistribution of primary arylsilanes to secondary arylsilanes. More significantly, this complex also effectively catalyzes the cross-coupling between electron-withdrawing substituted primary arylsilanes and electron-donating substituted primary arylsilanes to secondary arylsilanes containing two different aryls. DFT calculation indicates that the reaction always involve the exothermic formation of a hypervalent silicon upon facile addition of PhSiH3 to the Yb-E (E = C, H) bond. This hypervalent compound can easily either generate directly the Yb-Ph complex, or indirectly through the formation of Yb-H, that is the key complex for the formation of Ph2SiH2.

Metal-free hydrogen evolution cross-coupling enabled by synergistic photoredox and polarity reversal catalysis

A synergistic combination of photoredox and polarity reversal catalysis enabled a hydrogen evolution cross-coupling of silanes with H2O, alcohols, phenols, and silanols, which afforded the corresponding silanols, monosilyl ethers, and disilyl ethers, respectively, in moderate to excellent yields. The dehydrogenative cross-coupling of Si-H and O-H proceeded smoothly with broad substrate scope and good functional group compatibility in the presence of only an organophotocatalyst 4-CzIPN and a thiol HAT catalyst, without the requirement of any metals, external oxidants and proton reductants, which is distinct from the previously reported photocatalytic hydrogen evolution cross-coupling reactions where a proton reduction cocatalyst such as a cobalt complex is generally required. Mechanistically, a silyl cation intermediate is generated to facilitate the cross-coupling reaction, which therefore represents an unprecedented approach for the generation of silyl cationviavisible-light photoredox catalysis.

Silylation of Aryl Halides with Monoorganosilanes Activated by Lithium Alkoxide

Lithium alkoxide activates a monoorganosilane to generate a transient LiH/alkoxysilane complex, which quickly reacts with aryl and alkenyl halides at 25 °C to deliver a diorganosilane product. Experimental and theoretical studies suggest that the reaction includes nucleophilic attack of LiH on the halogen atom of the organic halide to generate a transient organolithium/alkoxysilane intermediate, which undergoes quick carbon-silicon bond formation within the complex.

Tris(oxazolinyl)boratomagnesium-catalyzed cross-dehydrocoupling of organosilanes with amines, hydrazine, and ammonia

We report magnesium-catalyzed cross-dehydrocoupling of Si-H and N-H bonds to give Si-N bonds and H2. A number of silazanes are accessible using this method, as well as silylamines from NH3 and silylhydrazines from N2H4. Kinetic studies of the overall catalytic cycle and a stoichiometric Si-N bond-forming reaction suggest nucleophilic attack by a magnesium amide as the turnover-limiting step.