36735-58-7Relevant academic research and scientific papers
Photosensitized Intermolecular Carboimination of Alkenes through the Persistent Radical Effect
Bellotti, Peter,Glorius, Frank,Patra, Tuhin,Strieth-Kalthoff, Felix
, p. 3172 - 3177 (2020/02/05)
An intermolecular, two-component vicinal carboimination of alkenes has been accomplished by energy transfer catalysis. Oxime esters of alkyl carboxylic acids were used as bifunctional reagents to generate both alkyl and iminyl radicals. Subsequently, addition of the alkyl radical to an alkene generates a transient radical for selective radical–radical cross-coupling with the persistent iminyl radical. Furthermore, this process provides direct access to aliphatic primary amines and α-amino acids by simple hydrolysis.
Tandem Photoredox and Copper-Catalyzed Decarboxylative C(sp3)-N Coupling of Anilines and Imines Using an Organic Photocatalyst
Barzanò, Guido,Mao, Runze,Garreau, Marion,Waser, Jerome,Hu, Xile
supporting information, p. 5412 - 5416 (2020/07/14)
An organic photoredox catalyst, 4CzIPN, was used in combination with a copper catalyst, CuCl, to effect decarboxylative C(sp3)-N coupling. The coupling worked with both anilines and imines as nitrogen sources and could be used to prepare a variety of alkyl amines from readily available alkyl carboxylic acids.
Benzhydrylamine: An effective aminating agent for the synthesis of primary amines
Sun, Quan-Wei,Xing, Jun-De,Qin, Yu-Hong,Yin, Xu-Wen,Zhou, Yi
, p. 181 - 183 (2018/05/26)
Aldehydes, ketones, alkyl toluene-p-sulfonates and halides are converted into the corresponding primary amines with benzhydrylamine as a valuable ammonia synthon in moderate to excellent yields.
Mechanism of the Pd-catalyzed decarboxylative allylation of α-imino esters: Decarboxylation via free carboxylate ion
Li, Zhe,Jiang, Yuan-Ye,Yeagley, Andrew A.,Bour, James P.,Liu, Lei,Chruma, Jason J.,Fu, Yao
, p. 14527 - 14538 (2013/01/15)
The Pd-catalyzed decarboxylative allylation of α-(diphenylmethylene) imino esters (1) or allyl diphenylglycinate imines (2) is an efficient method to construct new C(sp3)-C(sp3) bonds. The detailed mechanism of this reaction was stud
Synthesis of homoallylic amines via the palladium-catalyzed decarboxylative coupling of amino acid derivatives
Burger, Erin C.,Tunge, Jon A.
, p. 10002 - 10003 (2007/10/03)
Protected homoallylic amines are synthesized by the decarboxylative coupling of α-amino acid derivatives. The catalytic C-C bond-forming reaction relies on the bioinspired decarboxylative metalation of α-amino acids to produce α-amino anion equivalents. The α-amino anion equivalents are intercepted by π-allyl palladium electrophiles to produce substituted homoallylic amines. Copyright
Free radical-mediated aryl amination and its use in a convergent [3 + 2] strategy for enantioselective indoline α-amino acid synthesis
Viswanathan, Rajesh,Prabhakaran, Erode N.,Plotkin, Michael A.,Johnston, Jeffrey N.
, p. 163 - 168 (2007/10/03)
The scope of aryl radical additions to the nitrogen of azomethines is described. Aryl, trifluoromethyl alkyl, and α,β-unsaturated ketimines engage in regioselective aryl-nitrogen bond formation via 5-exo cyclizations of an aryl radical to azomethine nitrogen. Selectivity for carbon-nitrogen over carbon-carbon bond formation is generally high (>95:5) and competes only with direct aryl radical reduction by stannane (0-10%). α-Ketoimines are a promising new class of carbon radical acceptors for which no competitive aryl radical reduction is observed. The reaction conditions are pH-neutral and are therefore among the mildest methods available for amination of an aromatic ring. The ketimines examined did not suffer from competitive reduction by stannane, offering an advantage over the use of diazo and azide functional groups as nitrogen sources for carbon radicals. The free radical-mediated aryl amination was sequenced with the O'Donnell phase transfer-catalyzed enantioselective alkylation strategy of glycinyl imine to provide either enantiomer of indoline α-amino acids with high ee. These new constrained phenyl alanine derivatives are now readily available for evaluation across a variety of applications.
Nonconventional carbon additions to azomethines. Aryl amination/idoline synthesis by direct aryl radical addition to azomethine nitrogen
Johnston, Jeffrey N.,Plotkin, Michael A.,Viswanathan, Rajesh,Prabhakaran, Erode N.
, p. 1009 - 1011 (2007/10/03)
(matrix presented) The generality of a new method for aryl amination has been defined. Ketimines derived from o-bromophenethylamine cyclize to the N-substituted indoline when treated with nBu3SnH and a radical initiator. The pH-neutral conditions tolerate base- and acid-sensitive functionality. The observed regioselectivity is nonconventional for addition reactions involving carbon radicals and carbon-heteroatom π-bonds.
