17138-79-3Relevant articles and documents
Organophotocatalytic ring opening/remote trifluoromethylselenolation of cycloalkanols
Pan, Fei,Shi, Yingbo,Yuan, Wanqiang,Zhang, Qingyao
supporting information, (2022/05/20)
An organophotocatalytic ring opening/remote trifluoromethylselenolation of cycloalkanols is reported. This reaction proceeds the radical ring-opening in a photocatalytic system without metal catalysis under mild conditions, followed by the formation of the remote C(sp3)-SeCF3 bond in the presence of PhSO2SeCF3. The reaction brings out highly reactive to prepare trifluoromethylselenolated carbonyl compounds, suitable for a variety of aryl cyclic alcohols, while compatible with different ring systems with high yield, including 26 examples, the highest isolated yield of 93%.
Triphosgene and DMAP as Mild Reagents for Chemoselective Dehydration of Tertiary Alcohols
Ganiu, Moshood O.,Cleveland, Alexander H.,Paul, Jarrod L.,Kartika, Rendy
supporting information, p. 5611 - 5615 (2019/08/01)
The utility of triphosgene and DMAP as mild reagents for chemoselective dehydration of tertiary alcohols is reported. Performed in dichloromethane at room temperature, this reaction is readily tolerated by a broad scope of substrates, yielding alkenes preferentially with the (E)-geometry. While formation of the Hofmann products is generally favored, a dramatic change in alkene selectivity toward the Zaitzev products is observed when the reaction is carried out in dichloroethane at reflux.
Enantioselective Oxy-Heck–Matsuda Arylations: Expeditious Synthesis of Dihydrobenzofuran Systems and Total Synthesis of the Neolignan (?)-Conocarpan
Silva, Allan R.,Polo, Ellen C.,Martins, Nelson C.,Correia, Carlos Roque D.
, p. 346 - 365 (2018/01/26)
This work discloses the first examples of an effective enantioselective oxy-Heck–Matsuda reaction using a variety of styrenic olefins to generate chiral dihydrobenzofurans. The reaction proceeds in moderate to good yields, with high trans diastereoselectivity (up to 20:1) in enantioselectivities up to 90:10 using the N,N-ligand pyrimidine-bisoxazoline (PyriBox). The oxy-Heck–Matsuda reactions were carried out under mild conditions and rather low catalyst loadings. The feasibility and practicality of the process is demonstrated by a concise total synthesis of the neolignan (?)-conocarpan. X-ray diffraction of an advanced brominated intermediate in the route to (?)-conocarpan has allowed the unequivocal assignment of the absolute stereochemistry of the oxy-Heck–Matsuda aryldihydrobenzofuran products. A rationale for the mechanism operating in these enantioselective oxy-Heck–Matsuda reactions is also presented. (Figure presented.).
