18676-82-9

Upstream product

• 1631-83-0 diphenylsilyl chloride 
• 536-74-3 phenylacetylene 
• 775-12-2 diphenylsilane 

Downstream Products

• 74203-39-7 (3r,5r,7r)-1-(phenylethynyl)adamantane 

Relevant academic research and scientific papers

Dehydrogenative Coupling of Terminal Alkynes with O/N-Based Monohydrosilanes Catalyzed by Rare-Earth Metal Complexes

Newly synthesized rare-earth metal alkyl complexes bearing a tripyrrolyl ligand act as excellent precatalysts for the cross-dehydrogenative coupling between various terminal alkynes and O/N-based monohydrosilanes of HSi(OEt)3/HSi(NMe2)3, leading to the formation of a variety of alkoxysilylalkyne and aminosilylalkyne derivatives in good to high yields. The precatalysts LRE(CH2SiMe3)(thf)2 (RE = Y(1a), Er(1b), Yb(1c), L = 2,5-[(2-C4H3N)CPh2]2(C4H2NMe), thf = tetrahydrofuran) were easily prepared in high yields via the reactions of RE(CH2SiMe3)3(thf)2 with the proligand H2L in a single step. Mechanistic studies reveal that treatment of 1 with phenylacetylene could generate the active catalytic species: dinuclear rare-earth metal alkynides (L(thf)n[RE(μ-CCPh)]2L) (RE = Y(5a), n = 1; Yb(5c), n = 0), which could react with HSi(OEt)3 to produce the coupling product 4aa and the dinuclear rare-earth metal hydrides (L (thf)[RE(μ-H)]2L) (RE = Y(6a); Yb(6c)). By contrast, prior treatment of 1c with HSi(OEt)3 proceeds via cleavage of the Si-O bond to produce the dinuclear ytterbium alkoxide (LYb(μ-OEt))2 7c, which is inert in the dehydrogenative coupling reaction. The results of the mechanistic studies are consistent with the observation that the reaction is greatly influenced by the addition sequence of precatalyst/alkynes/silanes.

B(C6F5)3/Amine-Catalyzed C(sp)?H Silylation of Terminal Alkynes with Hydrosilanes: Experimental and Theoretical Studies

Transition metal catalyzed C?H functionalization of organic compounds has proved to be a useful atom-efficient strategy in organic synthesis. In contrast, main-group-element-based catalytic processes for C?H functionalization have remained underexplored t

Sodium triethylborohydride as a catalyst for the dehydrogenative silylation of terminal alkynes with hydrosilanes

The first example of sodium triethylborohydride-catalyzed C(sp)-H bond silylation is reported. The reaction of aromatic and aliphatic alkynes with aromatic hydrosilanes and hydrosiloxanes proceeded in a highly selective manner to afford dehydrocoupling pr

Silicon-tethered strategy for copper(I)-catalyzed stereo- and regioselective alkylboration of alkynes

Stereoselective silicon-tethered alkylboration of alkynes in the presence of a copper(I) catalyst and a diboron reagent provided the corresponding cyclic alkenylboronates in high yields (up to 99% yield) with excellent regio- and syn-selectivities (E/Z =

Unusual tandem alkynylation and trans-hydrosilylation to form oxasilacyclopentenes

(Chemical Equation Presented) An unusual tandem reaction sequence to form oxasilacyclopentenes from carbonyls and alkynylsilanes in the presence of a catalytic amount of nucleophilic initiator has been discovered. The reaction proceeds readily at room tem

Dehydrogenative coupling between hydrosilanes and alkynes catalyzed by alkoxides, alkylmetals, and metalamides

The selective dehydrogenative coupling reaction between phenylsilane and ethynylbenzene occurred in the presence of some homogeneous base catalysts such as alkoxides, alkyl compounds, and the amides of alkali metals or barium. The order of the catalytic activities was Ba(OR)2 > LiN(SiMe3)2 ～ n -BuLi > LiOEt. Barium alkoxide showed the highest activity and selectivity for the reaction, and gave the polymer poly[(phenylsilylene)ethynylene-1,3-phenyleneethynylene] in the reaction of phenylsilane with m-diethynylbenzene. The correlation between the catalytic activities and the catalyst basicities was discussed, and a reaction mechanism involving both the metal acetylide and the metal hydride was proposed.

Copper(I) chloride catalyzed cross-dehydrocoupling reactions between silanes and ethynyl compounds. A new method for the copolymerization of silanes and alkynes

In the presence of an amine, copper(I) chloride is an effective catalyst for the cross-dehydrocoupling of silanes with alkynes.The reactions proceed at useful rates above 100 deg C, but rates drop dramatically on going from 1o to 2o