17751-50-7Relevant academic research and scientific papers
Metal-Free Aminomethylation of Aromatic Sulfones Promoted by Eosin Y
Thierry, Thibault,Pfund, Emmanuel,Lequeux, Thierry
, p. 14826 - 14830 (2021/10/01)
A metal-free α-aminomethylation of heteroaryls promoted by eosin Y under green light irradiation is reported. A large variety of α-trimethylsilylamines as precursor of α-aminomethyl radical species were engaged to functionalize sulfonyl-heteroaryls following a Homolytic Aromatic Substitution (HAS) pathway. This method has provided a range of α-aminoheteroaryl compounds including a functionalized natural product. The mechanism of this late-stage functionalization of aryls was investigated and suggests the formation of a sulfonyl radical intermediate over a reductive quenching cycle.
Selective Heteroaryl N-Oxidation of Amine-Containing Molecules
Dyer, Robert M. B.,Hahn, Philip L.,Hilinski, Michael K.
supporting information, p. 2011 - 2014 (2018/04/16)
The first examples of nonenzymatic N-oxidation of heteroarenes in the presence of amines are reported. Pyridine, quinoline, and isoquinoline N-oxides are selectively formed in the presence of more reactive aliphatic and alicyclic amines by use of an in situ protonation strategy and an iminium salt organocatalyst. Application to late-stage functionalization that mimics phase 1 metabolism of small-molecule drugs is also demonstrated.
Simple Metal-Free Direct Reductive Amination Using Hydrosilatrane to Form Secondary and Tertiary Amines
Varjosaari, Sami E.,Skrypai, Vladislav,Suating, Paolo,Hurley, Joseph J. M.,Lio, Ashley M. De,Gilbert, Thomas M.,Adler, Marc J.
supporting information, p. 1872 - 1878 (2017/06/09)
This work describes the use of cheap, safe, and easy-to-handle hydrosilatrane as the reductant in direct reductive amination reactions. This efficient method enables a facile, metal-free access to secondary and tertiary amines from a wide range of aldehydes and ketones, with the synthesis of tertiary amines requiring no additives at all. This reaction demonstrates excellent functional group tolerance, chemoselectivity, and scalability. (Figure presented.).
Palladium-Catalyzed Benzylic C-H Arylation of Azaarylmethylamines
Kim, Byeong-Seon,Jiménez, Jacqueline,Gao, Feng,Walsh, Patrick J.
supporting information, p. 5788 - 5791 (2015/12/11)
A direct C-H functionalization approach to produce aryl(azaaryl)methylamines from azaarylmethylamines without directing groups is described. Under conditions where the azaarylmethylamines' C-H is reversibly deprotonated, a Pd(OAc)2/NIXANTPHOS-b
Synthesis, structures of (aminopyridine)nickel complexes and their use for catalytic ethylene polymerization
Lin, Ya-Chi,Yu, Kuo-Hsuan,Lin, Ya-Fan,Lee, Gene-Hsiang,Wang, Yu,Liu, Shiuh-Tzung,Chen, Jwu-Ting
experimental part, p. 6661 - 6670 (2012/08/08)
A series of α-aminopyridines in the form of (2,6-C6H 3N)(R1)(CHR2NR3R4) (R1 = R2 = H R3 = H R4 = iPr (L1a), R4 = tBu (L1b), R4 = Ph (L1c), R4 = 2,6-Me2C6H3 (L1d), R4 = 2,6-iPr2C6H3 (L1e), R1 = R2 = H R3 = R4 = Et (L1f), R1 = H R2 = Me R3 = H R4 = iPr (L2a), R4 = Ph (L2c), R4 = 2,6-Me 2C6H3 (L2d), R4 = 2,6- iPr2C6H3 (L2e), R1 = Me R2 = H R3 = H R4 = 2,6-iPr 2C6H3 (L3e)) and β-aminopyridines in the form of (2-C6H4N)(CH2CH2NR 1R2) (R1 = H R2 = iPr (4a), R2 = tBu (L4b), R1 = R2 = Et (L4f)) have been prepared. Their corresponding halonickel complexes 1a-4f are synthesized by ligand substitution from (DME)NiBr2 and the molecular structures are characterized. Four types of coordination modes include four-coordinate mononuclear species with one ligand, five-coordinate mononuclear species with two ligands, five-coordinate dinuclear species with two ligands, and a six-coordinate polymeric framework were determined by X-ray crystallography. Using methylaluminoxanes (MAO) as the activator, the nickel complexes can catalyze ethylene polymerization under moderate pressure and ambient temperature. The activity reaches 105 g PE mol-1 Ni h. The PE products with high branching and high crystallinity have M n ～ 103 with PDI 2.
SYNTHESIS OF 2-AMINOMETHYLPYRIDINES FROM AMINONITRILES AND ACETYLENE
Ivanov, A. P.,Levin, D. Z.,Mortikov, E. S.,Promonenkov, V. K.
, p. 566 - 570 (2007/10/02)
2-Aminomethylpyridines were synthesized from α-aminonitriles containing various substitutents at the α-carbon atom and acetylene at elevated pressures and temperatures in the presence of η5-dicyclopentadienylcobalt (cobaltocene) as catalyst.The
208. Aminierende reduktive Kupplung aromatischer Aldehyde mit niedervalenten Titan-Reagenzien zu 1,2-Diarylethylendiaminen
Betschart, Claudia,Seebach, Dieter
, p. 2215 - 2231 (2007/10/02)
In a novel McMurry-type one-pot reaction, aromatic aldehydes and secondary amines are coupled to give the N,N,N',N'-tetralkyl-1,2-diarylethylendiamines 1-22 (Table 3).To this end, a lithium dialkylamide is added to an aromatic aldehyde to give the adduct B which is then treated with 1 equiv. of TiCl4 to yield a coloured suspension of a reagent synthetically equivalent to a iminium salt (C/D in Scheme 4).After treatment with a low-valent Ti reagent which is prepared by reduction of TiCl4 with either K or, preferably, Mg, the coupling products are isolated in 23 to 81 percent yield as a 1:1 mixture of the diastereoisomers (meso- and rac-form).These are separated either by chromatography or by crystallization and characterized.
