3145-76-4Relevant articles and documents
Magid et al.
, p. 4921 (1969)
Mild Ring-Opening 1,3-Hydroborations of Non-Activated Cyclopropanes
Wang, Di,Xue, Xiao-Song,Houk, Kendall N.,Shi, Zhuangzhi
supporting information, p. 16861 - 16865 (2018/11/27)
The Brown hydroboration reaction, first reported in 1957, is the addition of B?H across an olefin in an anti-Markovnikov fashion. Here, we solved a long-standing problem on mild 1,3-hydroborations of non-activated cyclopropanes. A three-component system including cyclopropanes, boron halides, and hydrosilanes has been developed for borylative ring-opening of cyclopropanes following the anti-Markovnikov rule, under mild reaction conditions. Density functional theory (M06-2X) calculations show that the preferred pathway involves a cationic boron intermediate which is quenched by hydride transfer from the silane.
Cyclopropanation of alkenes with CH2I2/Et3Al by the phase-vanishing method based on fluorous phase screen
Matsubara, Hiroshi,Tsukida, Masaaki,Yasuda, Shinji,Ryu, Ilhyong
scheme or table, p. 951 - 954 (2009/04/04)
Phase-vanishing (PV) method using perfluorohexanes as a screen phase was applied to cyclopropanation reactions with CH2I2/Et2Zn and CH2I2/Et3Al. When Et3Al was used as a carbenoid generator, the reaction proceeded smoothly and desired cyclopropane derivatives were obtained in high yield. The PV cyclopropanation took 2 or 3 days to complete, however, reduction of reaction time by a factor of 2-3 was also achieved by vigorous stirring after the bottom CH2I2 layer disappeared.
