185989-92-8

Upstream product

• 629-05-0 n-octyne 
• 185990-03-8 dimethylphenyl(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)silane 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 3839-31-4 dimethyl(phenyl)silyl lithium 
• 1243241-40-8 2-[(1Z)-2-bromo-1-octen-1-yl]-4,4,5,5-tetramethyl 1,3,2-dioxaborolane 
• 67-63-0 isopropyl alcohol 
• 166329-94-8 (bis(diethylamino)-boranyl)dimethylphenylsilane 

Relevant academic research and scientific papers

(N-Heterocyclic Carbene)2-Pd(0)-Catalyzed Silaboration of Internal and Terminal Alkynes: Scope and Mechanistic Studies

Pd(ITMe)2(PhC≡CPh) acts as a highly reactive precatalyst in the silaboration of terminal and internal alkynes to yield a number of known and novel 1-silyl-2-boryl alkenes. Unprecedented mild reaction temperatures for terminal alkynes, short reaction times, and low catalytic loadings are reported. During mechanistic studies, cis-Pd(ITMe)2(SiMe2Ph)(Bpin) was directly synthesized by oxidative addition of PhMe2SiBpin to Pd(ITMe)2(PhC≡CPh). This represents a very rare example of a (silyl)(boryl)palladium complex. A plausible catalyst decomposition route was also examined.

Ligand-Dependent-Controlled Copper-Catalyzed Regio- And Stereoselective Silaboration of Alkynes

A copper-catalyzed highly regio- and stereoselective silaboration of alkynes was developed. In this work, direct cis-difunctionalization of alkynes was realized with silaboronate reagent and copper catalyst in aprotic solvents. The regiodivergent silabora

In Situ Generation of Silylzinc by Si?B Bond Activation Enabling Silylzincation and Silaboration of Terminal Alkynes

A new protocol has been designed for the in situ generation of unstable Si?Zn species through the reaction of dialkylzinc, phosphine, and silylborane (Si?B). Successive reactions with various terminal alkynes using this protocol enabled highly controllable regio-/stereo-/chemoselective silylzincation and silaboration on demand without the need for a transition-metal catalyst.

Switch of regioselectivity in palladium-catalyzed silaboration of terminal alkynes by ligand-dependent control of reductive elimination

The regioselectivity in the addition of silylboronic esters to terminal alkynes can be switched by the choice of phosphorus ligands on the palladium catalysts. The silaboration proceeds with normal regisoselectivity in the presence of (η3-Csub

Silylboranes bearing dialkylamino groups on silicon as silylene equivalents: Palladium-catalyzed regioselective synthesis of 2,4-disubstituted siloles

Silylpinacolboranes bearing dialkylamino groups on the silicon atom served as synthetic equivalents of silylene in palladium-catalyzed reactions with terminal alkynes, leading to the formation of 2,4-disubstituted siloles in high yield. It was found that the amino group on the silicon atom was critically important for the reaction; no silole products were found in reactions using silylpinacolboranes carrying aryl, chloro, or alkoxy groups on the silicon atoms. Site-selective bromination of 1,1-dimethyl-2,4-diphenylsilole followed by Migita-Kosugi-Stille coupling with (arylalkynyl)tributylstannanes gave novel π-conjugated siloles with good total yields. Copyright

Regio- and stereoselective synthesis of (Z)-β-silylalkenylboranes by silaboration of alkynes catalyzed by palladium and platinum complexes

Addition of the silicon-boron bonds of (dimethylphenylsilyl)boranes having pinacol, catechol, and diethylamino groups on the boron across carbon- carbon triple bonds is effectively catalyzed by palladium complexes. The silaboration of a variety of terminal alkynes took place with almost complete regio- and stereoselectivity to afford (Z)-1-boryl-2-silylalkenes in high yields. The silaboration products were subjected to the palladium-catalyzed cross-coupling reaction with aryl iodide and rhodium-catalyzed conjugate addition to methyl vinyl ketone, giving β-silylstyrene derivatives and δ- silyl-γ,δ-unsaturated ketones, respectively, in high yields.

Regio- and stereo-selective silaboration of alkynes catalysed by palladium and platinum complexes

Addition of the silicon-boron bond across carbon-carbon triple bonds, i.e. silaboration is most effectively catalysed by a palladium(0)-tert-alkyl isocyanide complex to give (Z)-1-boryl-2-silyl alkenes with high regio- and stereo-selectivity, which are useful for synthesis of stereodefined alkenylsilanes.