Cross-dehydrogenative coupling for the intermolecular C–O bond formation

• Igor B. Krylov,
• Vera A. Vil’ and
• Alexander O. Terent’ev

Beilstein J. Org. Chem. 2015, 11, 92–146, doi:10.3762/bjoc.11.13

• [146]. The coupling reaction with N-hydroxyphthalimide (154b) was carried out using the NaI/aqueous t-BuOOH/KOH system instead of Bu4NI/t-BuOOH in decane [146]. The resulting activated esters 159 and 160 were isolated or used in the one-pot reaction with amines to prepare amides (Scheme 32). The

Metal-free aerobic oxidations mediated by N-hydroxyphthalimide. A concise review

• Lucio Melone and
• Carlo Punta

Beilstein J. Org. Chem. 2013, 9, 1296–1310, doi:10.3762/bjoc.9.146

• Abstract Since the beginning of the century, N-hydroxyphthalimide and related compounds have been revealed to be efficient organocatalysts for free-radical processes and have found ample application in promoting the aerobic oxidation of a wide range of organic substrates. When combined with different co

• the O2-mediated selective oxidation of organic compounds and looking for environmentally safe alternatives to metal catalysis. Keywords: autoxidation; free-radicals; metal-free; molecular oxygen; N-hydroxyphthalimide; Introduction The development of efficient and cheap catalytic systems for the

• detrimental for the selectivity of the process and they would not meet the standards of “green chemistry”. An alternative catalytic route is based on the use of N-hydroxy imides (NHIs), and in particular N-hydroxyphthalimide (NHPI), which have found ample application as ideal catalysts for the aerobic

Copper-catalyzed aerobic aliphatic C–H oxygenation with hydroperoxides

• Pei Chui Too,
• Ya Lin Tnay and
• Shunsuke Chiba

Beilstein J. Org. Chem. 2013, 9, 1217–1225, doi:10.3762/bjoc.9.138

• weak bond-dissociation enthalpies (i.e., tertiary alkyl C–H bonds, benzylic C–H bonds, etc.), by phthalimide N-oxyl radicals generated oxidatively from N-hydroxyphthalimide (NHPI), has been reported [20][21][22]. The resulting C-radicals could be trapped with molecular oxygen to form hydroperoxides. It

Thioester derivatives of the natural product psammaplin A as potent histone deacetylase inhibitors

• Matthias G. J. Baud,
• Thomas Leiser,
• Vanessa Petrucci,
• Mekala Gunaratnam,
• Stephen Neidle,
• Franz-Josef Meyer-Almes and
• Matthew J. Fuchter

Beilstein J. Org. Chem. 2013, 9, 81–88, doi:10.3762/bjoc.9.11

• hydroxylamine, followed by coupling with 6 using DCC and N-hydroxyphthalimide [27] as coupling reagents afforded thioacetate 8. The latter conditions were also applied to 5 and afforded thioacetate analogue 9. The isolated yields for products 8 and 9 were unoptimised, and our previous work suggests that these

• next step without further purification. To a solution of this crude oxime derivative in dioxane (10 mL/mmol) under argon was added DCC (1 equiv) and N-hydroxyphthalimide (1 equiv). After 2 hours of stirring at rt, 2-acetylsulfanylethylammonium chloride (6, 1 equiv) and triethylamine (2.1 equiv) were

• )ethyl ethanethioate (9) To a solution of acid 5 under argon in dioxane (5.5 mL/mmol) was added DCC (1 equiv), N-hydroxyphthalimide (1 equiv). After 2 hours of stirring at rt, 2-acetylsulfanylethylammonium chloride (6, 1 equiv) and triethylamine (2.1 equiv) were added and the resulting mixture was