193096-45-6

Upstream product

• 1504-58-1 3-Phenyl-2-propyn-1-ol 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 108-86-1 bromobenzene 
• 591-50-4 iodobenzene 
• 76782-82-6 tert-Butyldimethyl(prop-2-ynyloxy)silane 

Downstream Products

• 1226968-27-9 (Z)-3-(t-butyldimethylsilyloxy)-2-diphenylphosphinyl-1-phenyl-1-propene 
• 1235479-13-6 4-(((tert-butyldimethylsilyl)oxy)methyl)-2-methyl-3-phenylisoquinolin-1(2H)-one 
• 1259284-08-6 C₂₂H₂₅NO₂ 
• 1259284-06-4 C₂₃H₂₉NO₂Si 
• 1259284-20-2 C₂₁H₂₉NO₄Si 
• 1257846-50-6 3-((tert-butyldimethylsilyloxy)methyl)-1-methyl-4-phenylisoquinoline 
• 1257846-33-5 4-((tert-butyldimethylsilyloxy)methyl)-1-methyl-3-phenylisoquinoline 
• 1313370-68-1 methyl 2-(((tert-butyldimethylsilyl)oxy)methyl)-1,3-diphenylcycloprop-2-enecarboxylate 
• 1350770-50-1 C₂₅H₃₁NOSi 
• 1350770-49-8 3-(((tert-butyldimethylsilyl)oxy)methyl)-6-methyl-2,4-diphenylpyridine 
• 1385029-68-4 (R)-methyl 2-(((tert-butyldimethylsilyl)oxy)methyl)-1,3-diphenylcycloprop-2-enecarboxylate 
• 1566600-08-5 [1-benzyl-2-(tert-butyl-dimethylsilanyloxy)ethyl]-(4-methoxyphenyl)amine 
• 69404-95-1 tert-butyldimethyl(3-phenylpropoxy)silane 
• 100009-29-8 (E)-1-tert-butyldimethylsilyloxy-3-phenyl-2-propene 

Relevant academic research and scientific papers

Copper-catalyzed formal transfer hydrogenation/deuteration of aryl alkynes

A copper-catalyzed reduction of alkynes to alkanes and deuterated alkanes is described under transfer hydrogenation and transfer deuteration conditions. Commercially available alcohols and silanes are used interchangeably with their deuterated analogues as the hydrogen or deuterium sources. Transfer deuteration of terminal and internal aryl alkynes occurs with high levels of deuterium incorporation. Alkyne-containing complex natural product analogues undergo transfer hydrogenation and transfer deuteration selectively, in high yield. Mechanistic experiments support the reaction occurring through a cis-alkene intermediate and demonstrate the possibility for a regioselective alkyne transfer hydrodeuteration reaction.

Chemoselective Hydroboration of Propargylic Alcohols and Amines Using a Manganese(II) Catalyst

The first manganese-catalyzed hydroboration of propargylic alcohols and amines as well as internal alkynes is reported. High regio- and stereoselectivity is achieved by applying 2 mol % of a manganese precatalyst based on the readily accessible bis(imino)pyridine ligand and MnCl2 as metal source. Propargylic alcohols and amines, as well as symmetric internal alkynes, were efficiently converted into the corresponding functionalized alkenes, which can serve as important and valuable intermediates for further synthetic applications such as cross-coupling reactions.

Silver triflate-catalyzed cyclopropenation of internal alkynes with donor-/acceptor-substituted diazo compounds

Silver triflate was found to be an efficient catalyst for the cyclopropenation of internal alkynes using donor-/acceptor-substituted diazo compounds as carbenoid precursors. Highly substituted cyclopropenes, which cannot be synthesized directly via rhodium(II)-catalyzed carbenoid chemistry, can now be readily accessed.

Activation of vinyl iodides for the highly enantioselective addition to aldehydes

(Chemical Equation Presented) Mild and tolerant: Vinylzinc reagents were directly prepared from the reaction of vinyl iodides with ZnEt2 under mild reaction conditions. The compound (S)-1 was found to catalyze the addition of the vinylzinc reag

Palladium-catalyzed intermolecular decarboxylative coupling of 2-phenylbenzoic acids with alkynes via C-H and C-C bond activation

A novel protocol for palladium-catalyzed intermolecular formal [4 + 2] annulation of 2-phenylbenzoic acids with alkynes is described. Acridine is shown to be essential for the high reaction efficiency. Phenanthrene derivatives are formed in moderate to good yields without coupling (pseudo)halides or organometallic species.

Pt(0)-catalyzed alkynylation of aryl iodides with lithium alkynyltriisopropoxy borates

An efficient cross coupling reaction of various lithium alkynyltriiospropoxyborates with a wide array of aryl iodides was catalyzed by Pt(PPh3)4-CuI in DMF as a solvent. These cross coupling reactions are general and permit the new sp-sp2 carbon-carbon bond formation.

Efficient coupling reactions of lithium alkynyl(triisopropoxy)borates with aryl halides: Application to the antifungal terbinafine synthesis

Thermally stable lithium alkynyl(triisopropoxy)borates were reacted with several aryl halides in the presence of palladium catalysts to give the corresponding cross-coupling products in excellent yields. The present methodology has been successfully appli

Nonionic superbase-catalyzed silylation of alcohols

Herein we report a very effective and mild procedure for the silyl protection of a wide variety of substrate alcohols, including primary, secondary, allylic, propargylic, benzylic, hindered secondary, tertiary, acid-sensitive, and base-sensitive alcohols and also hindered phenols. The silylation reagent used is tert-butyldimethylsilyl chloride (TBDMSCl) and the catalyst is P(MeNCH2CH2)3N, 1b, both of which are commercially available. The reactions are carried out in acetonitrile from 24 to 40 °C and on rare occasions in DMF from 24 to 80 °C. The effect of solvent, catalyst concentration, and temperature and reaction time on the silylation of alcohols and the excellent compatibility of our method with a variety of functional groups is discussed. An efficient method for recycling the catalyst is also presented. Although representative primary alcohols, secondary alcohols, and phenols were silylated using the more sterically hindered reagent tert-butyldiphenylsilyl chloride (TBDPSCl) in the presence of lb as a catalyst, tertiary alcohols were recovered unchanged.