Radical addition of ethers to alkenes under dioxygen catalyzed by N-hydroxyphthalimide (NHPI)/Co(OAc)2

Efficient metal-free oxidation of ethylbenzene with molecular oxygen utilizing the synergistic combination of NHPI analogues

“…N-hydroxyphthalimide (NHPI), a powerful organocatalyst, has attracted increasing attention in the last decades due to its established high efficiencies in oxidation studies [3][4][5][6][7][8][9][10]. Since Ishii and coworkers developed NHPI/metallic salts systems to promote the oxidation of various organic compounds with molecular oxygen [11][12][13][14], considerable efforts have been made to develop many catalytic systems containing NHPI or its derivatives towards the oxidation of various substrates [15][16][17][18][19][20][21][22]. Initiators, especially metal-based ones, are necessary to achieve the good catalytic performance of NHPI-based catalytic systems.…”

Mn(III)-Initiated Facile Oxygenation of Heterocyclic 1,3-Dicarbonyl Compounds

“…A similar degradation was also observed in the reaction of the hydroperoxides 2c , 2g (entries 10 and 11), the barbituric acid 5b and the hydroperoxide 6b (entries 12–17). Therefore, we could draw the conclusion that the transformation of hydroperoxides 2 and 6 into their corresponding alcohols 9 and 10 was due to a similar redox reactions using copper salt which has been extensively studied [ 69 , 70 , 71 ]. If the Mn(III) and Ce(IV) would function such as Cu(II), the mechanism of the degradation might be depicted in Scheme 7 .…”

Photocatalytic Synthesis of Oxetane Derivatives by Selective CH Activation

“…On the other hand, carbene insertion is unselective and ring enlargement or ring opening usually accompany this process making this approach unpractical 10. Activation of the CH bonds by using a radical initiator and trapping of the resulting α‐oxy radical by an electron‐poor olefin would seem a more appealing approach, but has been reported only in a few cases,11 starting from parent oxetane by activation via Et 3 B/O 2 ,11c NHPI/Co(OAc) 2 ,11d or benzoyl peroxide11a (but only with the oxetane as solvent). Furthermore, this approach is discouraged by the high activation energy for H abstraction from oxetanes measured with the sulfate radical anion,12 although the BDE (bond dissociation energy) for the C2H bond in oxetane (92.6 kcal mol −1 ) was calculated to be very similar to that of THF (92.8 kcal mol −1 ) 12…”