A mild and efficient H2O2 oxygenation of N-heteroaromatic compounds to the amine N-oxides and KI deoxygenation back to the tertiary amine with hexaphenyloxodiphosphonium triflate

Khodaei, Mohammad Mehdi; Alizadeh, Abdolhamid; Hezarkhani, Hadis Afshar

doi:10.1007/s13738-018-1381-4

Cited by 3 publications

(1 citation statement)

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“…As mild Lewis bases, pyridine N-oxides can result in activating Lewis acid parts of molecules and also increasing the reactivity of nucleophilic part toward different reactions with electrophiles. [115][116][117][118] Pyridines have been highly significant in catalyzing reactions, as reported in a study by Yoshida and coworkers. In this regard, they reported that when TBDPSCl, DIPEA, and pyrrolidinopyridine N-oxide (PPYO) catalyst are combined, it would bring about silylating different secondary alcohols in CH 2 Cl 2 at r.t. with excellent yields.…”

Section: N-oxides Catalyzed the Silylation Of Hydroxyl Groupsmentioning

confidence: 82%

Recent advances in catalytic silylation of hydroxyl‐bearing compounds: A green technique for protection of alcohols using Si–O bond formations

Ashraf

Liu

et al. 2020

Applied Organom Chemis

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The development of catalytic silylation of alcohols under ambient reaction conditions plays an important role in organic synthesis. New silyl groups and methods for their introduction and removal are constantly being developed and offer chemists a wider range of options. In recent years, silyl protecting groups have been given expanded roles beyond their traditional use of temporarily rendering inactive alcohols. As silyl ether can be further converted to the parent alcohols in acidic conditions, silylation of alcohols can be regarded as an alternative method for hydroxyl protection under ambient reaction conditions. Merging the silyl protection/deprotection of alcohols with such modern methodologies, as green chemistry and nanoscience, has added additional value to these temporary components of synthetic intermediates. This review describes the historical background of the trimethylsilyl ethers preparation from alcohols using catalytic complexes and also the transformation of trimethylsilyl ethers into alcohol-containing compounds via deprecation techniques.

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Section: N-oxides Catalyzed the Silylation Of Hydroxyl Groupsmentioning

confidence: 82%