278168-74-4Relevant academic research and scientific papers
Cu-Photoredox-catalyzed C(sp)-C(sp3) coupling of redox-active esters with terminal alkynes
Zhang, Dayong,Zhang, Yajing
supporting information, p. 4479 - 4483 (2020/10/20)
Visible-light-induced C(sp)-C(sp3) coupling of redox-active esters with terminal alkynes has been developed. The activation of carboxylic acids as their redox-active ester derivatives was important for this decarboxylative alkynylation. The strategy established here facilitates the straightforward introduction of triple-bonded functional groups and avoids additional photocatalysts. A wide range of primary, secondary and tertiary acids can be converted into the target products; so this reaction exhibits a broad substrate scope and tolerance of functional groups. Mechanistic experiments suggested that this reaction may undergo a radical process. Under mild reaction conditions, a copper acetylide ligand as a photocatalyst delivered an electron to redox-active ester derivatives, and generated alkyl radicals. The radicals reacted with Cu(ii) to deliver a Cu(iii) complex, and then reductive elimination gave the products.
Application of Hantzsch Ester and Meyer Nitrile in Radical Alkynylation Reactions
Liu, Xu,Liu, Ruoyu,Dai, Jie,Cheng, Xu,Li, Guigen
supporting information, p. 6906 - 6909 (2018/10/25)
The first example of constructing a Csp3-Csp bond with substituted Hantzsch ester and Meyer nitrile is reported. When benziodoxole-activated alkyne was applied as the alkynyl donor, products containing Csp3-Csp bonds involving primary, secondary, and tertiary carbon centers were achieved in up to 97% yields. K2S2O8 was the optimum radical initiator in this reaction.
Gold(I)-catalyzed arylmethylation of terminal alkynes
Li, Changkun,Li, Weibin,Wang, Jianbo
supporting information; experimental part, p. 2533 - 2535 (2009/07/26)
AuCl/AgOTf catalyzes the reaction of terminal alkynes with aryl trichloroacetimidate to afford arylmethylation products in moderate to good yields.
Lewis acid catalyzed propargylation of arenes with O-propargyl trichloroacetimidates: Synthesis of 1,3-diarylpropynes
Li, Changkun,Wang, Jianbo
, p. 7431 - 7434 (2008/02/11)
(Chemical Equation Presented) The BF3·OEt 2-catalyzed Friedel-Crafts propargylation of aromatic compounds with O-propargyl trichloroacetimidates is highly efficient and affords 1,3-diarylpropyne derivatives in good yields.
Catalytic synthesis of allenes via isomerization of alkynes under phase- transfer catalyzed conditions
Oku, Makoto,Arai, Shigeru,Katayama, Kimiko,Shioiri, Takayuki
, p. 493 - 494 (2007/10/03)
Catalytic isomerization of alkynes to allenes under phase-transfer catalyzed conditions is described. Commercially available quaternary ammonium salt such as tetrahexylammonium bromide acts as a very effective promoter to accelerate the reaction under mil
