10419-44-0Relevant academic research and scientific papers
Reactions of salicylaldehyde with tris(pentafluorophenyl)silanes and secondary amines
Dilman,Arkhipov,Belyakov,Struchkova,Tartakovsky
, p. 517 - 522 (2006)
Reactions of tris(pentafluorophenyl)silanes RSi(C6F 5)3 with salicylaldehyde and secondary amines were studied. The reactions afforded α-pentafluorophenyl-substituted amines. Silanes RSi(C6F5)3 (R = Me, Ph, C 6F5, CH2CH=CH2, and CH=CH 2) were found to be efficient reagents for transfer of the C 6F5 group to the iminium cation generated from salicylaldehyde and amine. However, tris(pentafluorophenyl)phenylethynyl-and tris(pentafluorophenyl)silanes were not able to serve as a source of a fluorinated substituent because of competitive transfer of acetylenide fragment or hydride.
Anionic ortho-fries rearrangement, a facile route to arenol-based mannich bases
Assimomytis, Nikos,Sariyannis, Yiannis,Stavropoulos, Georgios,Tsoungas, Petros G.,Varvounis, George,Cordopatis, Paul
, p. 2777 - 2782 (2009)
Phenol and 1-naphthol-based carbamates undergo the anionic ortho-Fries rearrangement to their corresponding amides. Bulky substitution at position 8 of 1-naphthol-based carbamates makes the rearrangement an exclusive reaction, even at -90 C, under a variety of conditions. The amides can be efficiently reduced to the corresponding Mannich bases. A novel route to 7-[(dialkylamino)methyl]-8- hydroxy-1-naphthaldehydes is presented.
Br?nsted acid catalysed chemo- andortho-selective aminomethylation of phenol
Li, Dongdong,Liu, Lu,Peng, Dan,Tang, Zhiqiong,Yue, Yidi
supporting information, p. 5777 - 5781 (2021/07/12)
We have developed a Br?nsted acid catalysed highlyortho-selective functionalization of free phenols with readily availableN,O-acetals under mild conditions, furnishing various corresponding aminomethylated phenol products in moderate to excellent yields. The salient features of this transformation include mild conditions, good substrate scope, excellentortho-selectivity, high efficiency, and ease of further transformation.
Aluminum Complexes of Monopyrrolidine Ligands for the Controlled Ring-Opening Polymerization of Lactide
Beament, James,Mahon, Mary F.,Buchard, Antoine,Jones, Matthew D.
supporting information, p. 1719 - 1724 (2018/06/18)
In this paper we report the full characterization (solution-state NMR spectroscopy and solid-state structures) of a series of Al(III) half-salan complexes and their exploitation for the ring-opening polymerization of rac-lactide. Depending on the ligand e
The modified-Mannich reaction: Conversion of arylboronic acids and subsequent coupling with paraformaldehyde and amines toward the one-pot synthesis of Mannich bases and benzoxazines
Liu, Juan,Yuan, Gaoqing
supporting information, p. 1470 - 1473 (2017/03/23)
A modified Mannich reaction has been developed for the synthesis of Mannich bases and benzoxazines via the oxidative hydroxylation of arylboronic acids and subsequent coupling with paraformaldehyde and amines in one pot. This modified Mannich reaction is easily carried out to afford the target products in good to excellent yields and tolerates a variety of functional groups.
Copper catalyzed oxidative deamination of Betti bases: An efficient approach for benzoylation/formylation of naphthols and phenols
Deb, Mohit L.,Pegu, Choitanya Dev,Borpatra, Paran J.,Baruah, Pranjal K.
, p. 40552 - 40559 (2016/05/24)
An efficient route for benzoylation or formylation of naphthols/phenols is developed via oxidative deamination of Betti bases. A copper salt catalyst with TBHP as an oxidant is used. Water is used as a reagent as well as solvent. The reaction proceeds through a regioselective radical pathway. Most importantly, the position of acylation is unambiguous. The method is also applicable to non-hydroxy substrates.
Mild and selective Et2Zn-catalyzed reduction of tertiary amides under Hydrosilylation conditions
Kovalenko, Oleksandr O.,Volkov, Alexey,Adolfsson, Hans
supporting information, p. 446 - 449 (2015/03/05)
Diethylzinc (Et2Zn) can be used as an efficient and chemoselective catalyst for the reduction of tertiary amides under mild reaction conditions employing cost-effective polymeric silane (PMHS) as the hydride source. Crucial for the catalytic activity was the addition of a substoichiometric amount of lithium chloride to the reaction mixture. A series of amides containing different additional functional groups were reduced to their corresponding amines, and the products were isolated in good-to-excellent yields.
Redox-neutral α-oxygenation of amines: Reaction development and elucidation of the mechanism
Richers, Matthew T.,Breugst, Martin,Platonova, Alena Yu.,Ullrich, Anja,Dieckmann, Arne,Houk,Seidel, Daniel
, p. 6123 - 6135 (2014/05/20)
Cyclic secondary amines and 2-hydroxybenzaldehydes or related ketones react to furnish benzo[e][1,3]oxazine structures in generally good yields. This overall redox-neutral amine α-C-H functionalization features a combined reductive N-alkylation/oxidative α-functionalization and is catalyzed by acetic acid. In contrast to previous reports, no external oxidants or metal catalysts are required. Reactions performed under modified conditions lead to an apparent reductive amination and the formation of o-hydroxybenzylamines in a process that involves the oxidation of a second equivalent of amine. A detailed computational study employing density functional theory compares different mechanistic pathways and is used to explain the observed experimental findings. Furthermore, these results also reveal the origin of the catalytic efficiency of acetic acid in these transformations.
Divergent reaction: Metal & oxidant free direct C-H aryloxylation and hydride free formal reductive N-benzylation of N-heterocycles
Mahato, Sujit,Haque, Md Ashraful,Dwari, Soumita,Jana, Chandan K.
, p. 46214 - 46217 (2015/02/19)
Metal, oxidant and other additive-free novel methods for direct C-H aryloxylation of aliphatic amines are developed. In the presence of excess amine, the course of the reaction was diverted, producing various arylmethylamines via hydride-free formal reductive amination. Involvement of a quinone methide intermediate was revealed from mechanistic studies. This journal is
Diastereoselective α-C-H functionalization of aliphatic N-heterocycles: An efficient route to ring fused oxazines
Mahato, Sujit,Haldar, Surajit,Jana, Chandan K.
supporting information, p. 332 - 334 (2014/01/06)
A novel method for direct C-H functionalization of saturated N-heterocycles allowing easy access to synthetically as well as biologically important and structurally diverse ring-fused oxazines is developed. The method is operationally simple and highly di
