116156-19-5Relevant articles and documents
Electro-alkynylation: Intramolecular Rearrangement of Trialkynylorganoborates for Chemoselective C(sp2)-C(sp) Bond Formation
Didier, Dorian,Lemke, Yannick,Music, Arif,Nuber, Constantin M.,Spie?, Philipp
supporting information, p. 4179 - 4184 (2021/06/27)
An alternative and complementary transformation for the synthesis of aryl- and heteroaryl-substituted alkynes is presented that relies on a chemoselective electrocoupling process. Tetraorganoborate substrates were logically designed and simply accessed by transmetalations using readily or commercially available organotrifluoroborate salts.
One-Pot Domino Synthesis of Diarylalkynes/1,4-Diaryl-1,3-diynes by [9,9-Dimethyl-4,5-bis(diphenylphosphino)xanthene] (Xantphos)–Copper(I) Iodide–Palladium(II) Acetate-Catalyzed Double Sonogashira-Type Reaction
Qiu, Shaozhong,Zhang, Caiyang,Qiu, Rui,Yin, Guodong,Huang, Jinkun
, p. 313 - 321 (2018/01/15)
The low loading combination of the complex [9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene] (Xantphos)copper(I) iodide and simple ligand-free palladium(II) acetate was found to be efficient for the domino synthesis of diarylalkynes by the reaction of aryl halides with trimethylsilylethynylene or bis(trimethylsilyl)acetylene in a single-step procedure. The unsymmetrical diarylalkynes can be obtained through a one-pot two-step approach. The reactions of aryl bromides with 1,4-bis(trimethylsilyl)butadiyne also furnished the corresponding 1,4-diaryl-1,3-diynes in a similar fashion. This route to diarylalkynes and 1,4-diaryl-1,3-diynes is complementary to previously reported synthetic procedures. (Figure presented.).
Copper-catalyzed aerobic oxidative transformation of ketone- Derived N-tosyl hydrazones: An entry to alkynes
Li, Xianwei,Liu, Xiaohang,Chen, Huoji,Wu, Wanqing,Qi, Chaorong,Jiang, Huanfeng
supporting information, p. 14485 - 14489 (2015/02/05)
A novel strategy involving Cu-catalyzed oxidative transformation of ketone-derived hydrazone moiety to various synthetic valuable internal alkynes and diynes has been developed. This method features inexpensive metal catalyst, green oxidant, good functional group tolerance, high regioselectivity and readily available starting materials. Oxidative deprotonation reactions were carried out to form internal alkynes and symmetrical diynes. Cross-coupling reactions of hydrazones with halides and terminal alkynes were performed to afford functionalized alkynes and unsymmetrical conjugated diynes. A mechanism proceeding through a Cu-carbene intermediate is proposed for the CC triple bond formation.