185989-92-8

Basic information

• Product Name: PhSiMe₂C(n-C₆H₁₃)CHB(pinacolato)
• Synonyms: PhSiMe₂C(n-C₆H₁₃)CHB(pinacolato)
• CAS NO: 185989-92-8
• Molecular Weight: 372.431
• Mol File: 185989-92-8.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: PhSiMe₂C(n-C₆H₁₃)CHB(pinacolato)(CAS DataBase Reference)
• NIST Chemistry Reference: PhSiMe₂C(n-C₆H₁₃)CHB(pinacolato)(185989-92-8)
• EPA Substance Registry System: PhSiMe₂C(n-C₆H₁₃)CHB(pinacolato)(185989-92-8)

Safety Data

• Hazardous Substances Data: 185989-92-8(Hazardous Substances Data)

Upstream product

• 629-05-0 n-octyne 
• 185990-03-8 dimethylphenyl(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)silane 
• 67-63-0 isopropyl alcohol 
• 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 
• 166329-94-8 (bis(diethylamino)-boranyl)dimethylphenylsilane 
• 76-09-5 2,3-dimethyl-2,3-butane diol 

Relevant articles and documents

(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.

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.

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