39884-48-5Relevant articles and documents
Remote C(sp3)-H Oxygenation of Protonated Aliphatic Amines with Potassium Persulfate
Lee, Melissa,Sanford, Melanie S.
supporting information, p. 572 - 575 (2017/02/10)
This letter describes the development of a method for selective remote C(sp3)-H oxygenation of protonated aliphatic amines using aqueous potassium persulfate. Protonation serves to deactivate the proximal C(sp3)-H bonds of the amine substrates and also renders the amines soluble in the aqueous medium. These reactions proceed under relatively mild conditions (within 2 h at 80 °C with amine as limiting reagent) and do not require a transition metal catalyst. This method is applicable to a variety of types of C(sp3)-H bonds, including 3°, 2°, and benzylic C-H sites in primary, secondary, and tertiary amine substrates.
Selective functionalization of amino acids in water: A synthetic method via catalytic C-H bond activation [17]
Dangel,Johnson,Sames
, p. 8149 - 8150 (2007/10/03)
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PROTECTION OF PRIMARY AND SECONDARY AMINES IN THE HYDROBORATION REACTION
Dicko, A.,Montury, M.,Baboulene, M.
, p. 6041 - 6044 (2007/10/02)
Trimethylsilyl groups are efficient to protect the N-H bonds of olefinic amines in the hydroboration reaction with BMS; deprotection is easily run with methanol and affords aminoorganoboranes which can be used without any oxydation.