61082-14-2Relevant articles and documents
Photocatalytic nucleophilic addition of alcohols to styrenes in Markovnikov and anti-Markovnikov orientation
Weiser, Martin,Hermann, Sergej,Penner, Alexander,Wagenknecht, Hans-Achim
, p. 568 - 575 (2015/06/08)
The nucleophilic addition of methanol and other alcohols to 1,1-diphenylethylene (1) and styrene (6) into the Markovnikov- and anti-Markovnikov-type products was selectively achieved with 1-(N,N-dimethylamino)pyrene (Py) and 1,7-dicyanoperylene-3,4:9,10-tetracarboxylic acid bisimide (PDI) as photoredox catalysts. The regioselectivity was controlled by the photocatalyst. For the reductive mode towards the Markovnikov-type regioselectivity, Py was applied as photocatalyst and triethylamine as electron shuttle. This approach was also used for intramolecular additions. For the oxidative mode towards the anti-Markovnikov-type regioselectivety, PDI was applied together with Ph-SH as additive. Photocatalytic additions of a variety of alcohols gave the corresponding products in good to excellent yields. The proposed photocatalytic electron transfer mechanism was supported by detection of the PDI radical anion as key intermediate and by comparison of two intramolecular reactions with different electron density. Representative mesoflow reactor experiments allowed to significantly shorten the irradiation times and to use sunlight as "green"light source.
A Convenient Method for the Preparation of Ethers from Epoxides. Trityl Hexafluoroantimonate-Catalyzed Sequential Reactions, Rearrangement and Reductive Condensation, of Epoxides
Harada, Tsunehiro,Mukaiyama, Teruaki
, p. 1901 - 1904 (2007/10/02)
In the presence of a catalytic amount of trityl hexafluoroantimonate, sequential reactions, rearrangement and reductive condensation, of epoxides proceed smoothly to give the corresponding ethers in fairly good yields.Trityl hexafluoroantimonate (5 molpercent) efficiently accelerates the above two sequential reactions.