1104516-50-8Relevant articles and documents
Electrochemistry-Enabled Ir-Catalyzed Vinylic C-H Functionalization
Yang, Qi-Liang,Xing, Yi-Kang,Wang, Xiang-Yang,Ma, Hong-Xing,Weng, Xin-Jun,Yang, Xiang,Guo, Hai-Ming,Mei, Tian-Sheng
supporting information, p. 18970 - 18976 (2019/12/04)
Synergistic use of electrochemistry and organometallic catalysis has emerged as a powerful tool for site-selective C-H functionalization, yet this type of transformation has thus far mainly been limited to arene C-H functionalization. Herein, we report the development of electrochemical vinylic C-H functionalization of acrylic acids with alkynes. In this reaction an iridium catalyst enables C-H/O-H functionalization for alkyne annulation, affording α-pyrones with good to excellent yields in an undivided cell. Preliminary mechanistic studies show that anodic oxidation is crucial for releasing the product and regeneration of an Ir(III) intermediate from a diene-Ir(I) complex, which is a coordinatively saturated, 18-electron complex. Importantly, common chemical oxidants such as Ag(I) or Cu(II) did not give significant amounts of the desired product in the absence of electrical current under otherwise identical conditions.
Rhodium(III)-catalysed decarbonylative coupling of maleic anhydrides with alkynes
Matsuda, Takanori,Suzuki, Kentaro
, p. 37138 - 37141 (2014/11/08)
A formal [5 - 1 + 2] annulation for the preparation of substituted α-pyrones is reported. The reaction involves the decarbonylative coupling of substituted maleic anhydrides with internal alkynes in the presence of a rhodium(III) catalyst and a copper(II)
Expedient synthesis of highly substituted α-pyrones from Baylis-Hillman adducts and their conversion to poly-substituted aromatics
Kim, Eun Sun,Kim, Ko Hoon,Kim, Sung Hwan,Kim, Jae Nyoung
scheme or table, p. 5098 - 5101 (2009/12/01)
An efficient synthetic protocol of fully substituted α-pyrones has been developed starting from the Baylis-Hillman adducts. Subsequent Diels-Alder reaction of the α-pyrones and DMAD produced poly-substituted aromatic compounds in high yields.