31776-90-6Relevant academic research and scientific papers
Palladium/P(t-Bu)3-catalyzed synthesis of aryl t-butyl ethers and application to the first synthesis of 4-chlorobenzofuran
Watanabe, Makoto,Nishiyama, Masakazu,Koie, Yasuyuki
, p. 8837 - 8840 (2007/10/03)
Pd/P(t-Bu)3 catalyzed reaction of aryl halides with sodium t-butoxide effectively to give aryl t-butyl ethers. The high catalytic activity realized the formation of aryl t-butyl ethers from not only electron-deficient aryl halides but also electron-rich aryl halides. Moreover, the first synthesis of 4-chlorobenzofuran was attained utilizing the selective mono-t-butoxylation of aryl dihalide.
Preparation of Didehydropyridines from (Trimethylsilyl)pyridines
Effenberger, Franz,Daub, Wolfgang
, p. 2119 - 2125 (2007/10/02)
Halogen-substituted (trimethylsilyl)pyridines 2, 3, 5-7 and trifluoromethylsulfonyloxy-substituted (trimethylsilyl)pyridines 9b, 11b are obtained from 2- and 3-halopyridines 1, 4 or hydroxypyridines 8, 10, and 12.Reactions of the 3- and 2-(trimethylsilyl)pyridines 2, 9b and 11b with bases in the presence of furans 15 give only protodesilylation or hydrolysis products but no indication is found for the formation of a 2,3-didehydropyridine. 3-Bromo-4-(trimethylsilyl)pyridine (5a) reacts with KOCMe3 in the presence of furan (15a) to give a mixture of products from which the isoquinoline derivative 20 and the tert-butoxypyridines 23, 24 are formed by addition to 3,4-didehydropyridine.Under comparable conditions far higher yields of 3,4-didehydropyridines are obtained by treatment of the 3-halo-2,4-bis(trimethylsilyl)pyridines 7 with strong bases. Key Words: Didehydropyridines, synthesis of
