1160112-01-5Relevant articles and documents
Dual ligand-promoted palladium-catalyzed nondirected C-H alkenylation of aryl ethers
Fu, Manlin,Liu, Jiang,Wang, Lei,Yin, Biao,Zhu, Qing
, p. 3293 - 3296 (2020)
Direct C-H functionalization of aryl ethers remains challenging owing to their low reactivity and selectivity. Herein, a novel strategy for nondirected C-H alkenylation of aryl ethers promoted by a dual ligand catalyst was demonstrated. This catalytic system readily achieved the highly efficient alkenylation of alkyl aryl ethers (anisole, phenetole, n-propyl phenyl ether, n-butyl phenyl ether and benzyl phenyl ether), cyclic aryl ethers (1,4-benzodioxan, 2,3-dihydrobenzofuran, dibenzofuran), and diphenyl oxides. Moreover, the proposed methodology was successfully employed for the late-stage modification of complex drugs containing the aryl ether motif. Interestingly, the compounds developed herein displayed fluorescent properties, which would facilitate their biological applications.
Carbonyl–Olefin Cross-Metathesis Through a Visible-Light-Induced 1,3-Diol Formation and Fragmentation Sequence
Pitzer, Lena,Sandfort, Frederik,Strieth-Kalthoff, Felix,Glorius, Frank
supporting information, p. 16219 - 16223 (2018/11/23)
A visible-light-mediated approach to carbonyl–olefin cross-metathesis is described. Photoinduced hole catalysis was used to promote the formation of 1,3-diols from aldehydes and styrenes, which were then readily fragmented under acidic conditions to form the cross-metathesis products. The use of 1,3-diols as intermediates, rather than the energetically more demanding oxetanes, provides a new, orthogonal mechanistic strategy for carbonyl–olefin cross-metathesis. Furthermore, this approach does not require any metals, ligands, or additives, and provides the products with high levels of E selectivity. A mechanistic rationale is provided and supported by both theoretical calculations and experiments. Additionally, a practical synthesis of a new acridinium-based photocatalyst, including full characterization, is presented.