1126896-40-9

Upstream product

• 536-50-5 CH₃C₆H₄CH(CH₃)OH 
• 536-74-3 phenylacetylene 
• 622-97-9 1-ethenyl-4-methylbenzene 
• 932-87-6 1-Bromo-2-phenylacetylene 
• 159755-12-1 1-(1-bromoethyl)-4-methylbenzene 

Relevant academic research and scientific papers

A Copper-Catalyzed Sonogashira Coupling Reaction of Diverse Activated Alkyl Halides with Terminal Alkynes Under Ambient Conditions

We describe a copper-catalyzed Sonogashira coupling reaction of alkyl halides with terminal alkynes under ambient conditions, efficiently providing a versatile tool for the construction of substituted alkynes. A new proline-based N,N,P-ligand is utilized to promote the transformation under a mild reaction condition. Diverse alkyl halides, such as primary and secondary (hetero)benzyl chlorides and bromides, secondary and tertiary α-bromo amides and propargylic bromide, are applicable to provide a wide array of alkynes. (Figure presented.).

Transmetalation of Alkylzirconocenes in Copper-Catalyzed Alkyl–Alkynyl Cross-Coupling Reactions

A simple copper-catalyzed alkyl–alkynyl cross-coupling strategy has been developed using the reaction between alkynyl bromides and alkylzirconocenes. The alkylzirconocenes were generated in situ via regioselective addition of Schwartz's reagent (ZrCp2HCl) on to alkenes. The reaction has a broad scope, a range of functionalized bromoalkynes and alkylzirconium reagents were successfully coupled, resulting in moderate to good yields of the desired internal alkynes. (Figure presented.).

Catalytic C-N bond alkynylation of N-benzylic sulfonamides with terminal alkynes

A new cross-coupling reaction of N-benzylic sulfonamides with terminal alkynes for the synthesis of internal alkynes is reported. In the presence of 5 mol% of (Tf)2NH/Bi(OTf)3 (1:1), a broad range of N-benzylic sulfonamides react smoothly with arylacetylenes to afford structurally diverse internal alkynes in moderate to excellent yields. We reasoned that vinyl cations could be formed by the regioselective attack of terminal alkynes with benzyl cations generated in situ from N-benzylic sulfonamides under acidic conditions, which then eliminated to form a carbon-carbon triple bond. An unprecedented synthesis of internal alkynes from N-benzylic sulfonamides and terminal alkynes has been developed through TfOH/Fe(OTf)3-catalyzed cleavage of C(sp3)-N bonds and C(sp)-H bonds. This protocol is compatible with a broad range of N-benzylic sulfonamides and arylacetylenes. Copyright

Indium(III) catalyzed direct sp3-sp C-C bond formation from alcohols and terminal alkynes

A simple and efficient indium(III)-catalyzed sp3-sp C-C bond formation reaction via direct coupling of alcohols with terminal alkynes has been developed under mild conditions without any ligand, base or additive, in which both of aromatic and aliphatic alkynes and various alcohols such as benzylic, allylic and propargylic alcohols can be tolerated. This simple reaction system provides an attractive approach to a large number of internal alkynes in moderate to good yields, and only generates H2O as the side product.