1453904-93-2Relevant academic research and scientific papers
Furans Accessed through Visible-Light-Mediated Oxidative [3+2] Cycloaddition of Enols and Alkynes
Shao, Ailong,Luo, Xu,Chiang, Chien-Wei,Gao, Meng,Lei, Aiwen
, p. 17874 - 17878 (2017)
Visible-light-mediated formation of furans though direct oxidative [3+2] cycloaddition of 1,3-diones and alkynes is described. This protocol provides a simple and mild route to poly-substituted furans in moderate-to-good yields. Preliminary mechanistic studies suggest that this reaction likely follows a radical addition/cyclization pathway.
De Novo synthesis of polysubstituted naphthols and furans using photoredox neutral coupling of alkynes with 2-bromo-1,3-dicarbonyl compounds
Jiang, Heng,Cheng, Yuanzheng,Zhang, Yan,Yu, Shouyun
supporting information, p. 4884 - 4887 (2013/10/08)
A conceptually new strategy has been described for the mild, practical, and environmentally friendly preparation of naphthols and furans using a visible-light promoted photoredox neutral approach. These reactions between accessible electron-deficient bromides and commercially available alkynes could be carried out at room temperature in good-to-excellent chemical yields without any external stoichiometric oxidants.
Chemoselectivity control: Gold(I)-catalyzed synthesis of 6,7-dihydrobenzofuran-4(5H)-ones and benzofurans from 1-(alkynyl)-7- oxabicyclo[4.1.0]heptan-2-ones
Wang, Tao,Shi, Shuai,Vilhelmsen, Mie Hojer,Zhang, Tuo,Rudolph, Matthias,Rominger, Frank,Hashmi, A. Stephen K.
, p. 12512 - 12516 (2013/09/23)
New and chemoselective gold(I)-catalyzed transformations of 1-(arylethynyl)-7-oxabicyclo[4.1.0]- heptan-2-ones were developed. Two completely different products - 6,7-dihydrobenzofuran-4(5H)-ones and benzofurans - could be obtained from the same starting material. The selectivity is determined by the ligand of the gold catalyst: triphenylphosphine delivers 6,7-dihydrobenzofuran-4(5H)-ones, and 1,3-bis(diisopropylphenyl)imidazol-2- ylidene leads to benzofurans. Eleven examples of each case are provided. The mechanistic suggestions for the pathways to both product types are supported by isotope labeling experiments. Complete chemoselectivity control of gold(I)-catalyzed transformations of 1-(arylethynyl)-7-oxabicyclo[4.1.0]heptan- 2-ones, which can be achieved by changing the ligand of the gold catalyst, allows two different products to be obtained from the same starting material, namely, 6,7-dihydrobenzofuran-4(5H)-ones and benzofurans (see scheme), both of which are potent building blocks for synthetic chemistry. IPr: 1,3-bis(diisopropylphenyl)imidazol-2-ylidene. Copyright
