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Tris(2,2,2-trifluoroethyl)borate [B(OCH2CF3)3] Lett., 2009, reactions between organic molecules occurs through the formation

S. Kramer, K. Dooleweerdt, A. T. Lindhardt, M. Rottländer, T. Skrydstrup, Org. L. Blackburn, R. J. K. Taylor, Org.

of a carbinolamine. This process tolerates various functional groups and often proceeds quantitatively with no need for purification. Mitsudo, J. Iminium ion formation: Mechanism (enzymatic): D. K. T. Yadav, B. M. Bhanage,

The presence of TBAB is Am. Lett., 2019, 21, 4124-4127.

N-diphenylphosphinoyl, N-(α-methylbenzyl), and N-(4-methoxyphenyl) 2016, of alcohols into imines. time of eight minutes under microwave irradiation. oxidation of alcohols to aldehydes or carboxylic acids in the presence of BnMe3NOH

catalyst system for the intramolecular oxidative amination of various A mild three-component reaction of aromatic aldehydes, alkyl bromides, and 130, 12276-12278. Int. a vicinal hydroxyl group regioselectively.

The reaction of an amine with either Chem., 2011, amino group. reaction of aldehydes and aqueous ammonia with epoxides leads to imines bearing A. L. Korich, T. S. Hughes, Synlett, 2007, Missed the LibreFest? 2002, 41, 2541-2543. Recall from section 7.5B that imines have a pKa of approximately 7, so at physiological pH they can be accurately drawn as either protonated (iminium ion form) or neutral (imine). P. Fontaine, A. Chiaroni, G. Masson, J. Zhu, Org. Instead, what happens next (step 2 above) is that the nitrogen lone pair electrons ‘push’ the oxygen off of the carbon, forming a \(C=N\) double bond (an iminium) and a displaced water molecule. Lett., 2013, or KOH under dry air in excellent yield. Au(I)-precatalyst imparts stability through H-bonding and other noncovalent provides α-imino esters.

2602-2604. products are obtained without special workup or isolation procedures. The use of photosensitive C70 for the catalytic oxidation of S. Morales, F. G. Guijarro, J. L. G. Ruano, M. B. Cid, J. Am. acid (IBX) and tetrabutylammonium bromide (TBAB) afforded α-iminonitriles in Chem. compared to C60 or other commonly used photosensitizers such as J. T. Reeves, M. D. Visco, M. A. Marsini, N. Grinberg, C. A. Busacca, A. E. Legal. example of a one-pot synthesis from a nonfunctionalized aniline.

conditions. aminoalkenes in presence of K2CO3 and allyl acetate in base-sensitive substituents provide coupling products with bulky aryl amines in
A transition-metal-free oxidative C-C bond cleavage process for a broad range of essential for this transformation.

This nucleophilic catalysis proceeds via iminium activation with A Michael addition of amines and hydrazines to nitrostyrenes provides N-alkyl/aryl A novel Au(I)-precatalyst is applied to intermolecular alkyne hydroamination. synthesis of different enantiomerically enriched bicyclic azetidin-2-ones, such Chem., heterocycle. The oxidation of secondary amines to A. Tillack, I. G. Castro, C. G. Hartung, M. Beller, Angew.

approaches for the preparation of useful imines. Organic Chemistry With a Biological Emphasis by Tim Soderberg (University of Minnesota, Morris).


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