170948-10-4Relevant articles and documents
A reversible safety-catch method for the hydrogenolysis of N-benzyl moieties
Johnson II, David C.,Widlanski, Theodore S.
, p. 8483 - 8487 (2007/10/03)
The benzyl groups of β-hydroxy-N-benzyl sulfonamides are labile toward hydrogenolysis-unlike N-benzyl sulfonamides lacking the β-hydroxy moiety. We find that N-acyl-N-benzyl sulfonamides undergo hydrogenolysis under very mild conditions. Based upon these observations, we developed a reversible safety-catch method using tert-butoxycarbonyl moieties to activate N-benzyl sulfonamides toward hydrogenolysis. We also explored the utility of the safety-catch activation method for other nitrogen-based functionality such as N-benzyl carboxamides, imides, and related functionality.
Reductive deprotection of allyl, benzyl and sulfonyl substituted alcohols, amines and amides using a naphthalene-catalysed lithiation
Alonso, Emma,Ramon, Diego J.,Yus, Miguel
, p. 14355 - 14368 (2007/10/03)
The reaction of different protected alcohols, amines and amides with lithium and a catalytic amount of naphthalene (4 mol %) in THF at low temperature leads to their deprotection under very mild reaction conditions, the process being in many cases chemoselective.
Synthesis and cathodic cleavage of a set of substituted benzenesulfonamides including the corresponding tert-butyl sulfonylcarbamates: pKa of sulfonamides
Nyasse, Barthelemy,Grehn, Leif,Ragnarsson, Ulf,Maia, Hernani L. S.,Monteiro, Luis S.,et al.
, p. 2025 - 2032 (2007/10/02)
From a series of substituted benzenesulfonic acids, most of which have previously been employed for the protection of amino functions and including a few such known to facilitate cleavage by acid, benzylamides 1a-k have been derived and studied.Initially their electrochemical cleavage potentials were determined by cyclic voltammetry in order to further explore selective deprotection within this substance group.In parallel, the corresponding tert-butyl sulfonylcarbamates 2a-k have also been prepared and studied.Among the sulfonamides investigated S-N bond cleavage was found to take place over a wide range of potentials from -1.67 to -2.64 V (excluding the nitro derivative), the most acid-labile groups requiring more negative potentials, whereas this cleavage was facilitated by 0.19-0.39 V for the sulfonylcarbamates.Small scale electolyses of 2 at controlled potential with determination of the cleavage products formed were subsequently performed.For the N-benzylbenzenesulfonamides, 1, the pKas in DMSO and in some cases also in water have been determined and found to be in the range 14.0-16.4 and 10.07-11.53, respectively.
Selective Cathodic Cleavage of Protected, Mixed Primary-Secondary Amines
Grehn, Leif,Maia, Hernaeni L. S.,Monteiro, Luis S.,Montenegro, M. Irene,Ragnarsson, Ulf
, p. 1501 - 1519 (2007/10/02)
This paper presents the results of an investigation aiming at exploiting the effect of a t-butoxycarbonyl (Boc) group for selective preparative cleavage of one of the protecting groups of fully protected, mixed primary-secondary amines.For this purpose on
