30979-60-3Relevant articles and documents
Poly(methylhydrosiloxane) as a green reducing agent in organophosphorus-catalysed amide bond formation
Hamstra, Daan F. J.,Lenstra, Danny C.,Koenders, Tjeu J.,Rutjes, Floris P. J. T.,Mecinovi?, Jasmin
supporting information, p. 6426 - 6432 (2017/08/10)
Development of catalytic amide bond formation reactions has been the subject of the intensive investigations in the past decade. Herein we report an efficient organophosphorus-catalysed amidation reaction between unactivated carboxylic acids and amines. Poly(methylhydrosiloxane), a waste product of the silicon industry, is used as an inexpensive and green reducing agent for in situ reduction of phosphine oxide to phosphine. The reported method enables the synthesis of a wide range of secondary and tertiary amides in very good to excellent yields.
The invention of radical reactions. 30. Diazirines as carbon radical traps. Mechanistic aspects and synthetic applications of a novel and efficient amination process
Barton, Derek H. R.,Jaszberenyi, Joseph Cs.,Theodorakis, Emmanouil A.,Reibenspies
, p. 8050 - 8059 (2007/10/02)
A number of diazirines were synthesized for the purpose of exploring the addition of a carbon radical to the nitrogen-nitrogen double bond. Carbon radicals, generated from the photolysis of the O-acyl derivatives of N-hydroxy-2-thiopyridone or via radical exchange from the corresponding organotellurides, were shown to add smoothly to the diazirines leading to imines 34. When 3-(trifluoromethyl)-3-phenyldiazirine (13) is used as the trap, the thus formed imines can be easily hydrolyzed to amines. A mechanism that involves dimerization of the diaziridinyl radicals 32 to produce tetraazo intermediates 33 is suggested in accord with variable temperature NMR data for the reaction. Proof for this mechanistic scheme was furthermore obtained by isolation and X-ray structure determination of 33d. The first X-ray structure of a 3-(trifluoromethyl)-3-aryldiazirine is also reported.
