132993-22-7Relevant articles and documents
High pressure organic chemistry; XI. A new convenient synthesis of aromatic amines from activated phenols
Kotsuki,Kobayashi,Suenaga,Nishizawa
, p. 1145 - 1147 (1990)
Aryl triflates containing electron-withdrawing substituents efficiently react with amines in refluxing acetonitrile or at 10 kbar pressure to give various aromatic amines.
First Study of the Thermal and Storage Stability of Arenediazonium Triflates Comparing to 4-Nitrobenzenediazonium Tosylate and Tetrafluoroborate by Calorimetric Methods
Bondarev, Alexander A.,Naumov, Evgeny V.,Kassanova, Assiya Zh.,Krasnokutskaya, Elena A.,Stankevich, Ksenia S.,Filimonov, Victor D.
supporting information, p. 2405 - 2415 (2019/10/11)
Herein, for the first time, using isothermal flow calorimetry and differential scanning calorimetry (DSC)/thermal gravimetric analysis (TGA), we have determined the thermal decomposition energies for the number of solid arenediazonium triflates comparing to 4-nitrobenzene tosylate and 4-nitrobenzentetrafluoroborate. The kinetics of thermal decomposition, activation energies, and half-lives of the studied diazonium salts (DSs) were found. Using gas chromatography-mass spectrometry (MS) and liquid chromatography-MS, we have elucidated the products formed during thermolysis of the investigated DSs. By density functional theory quantum chemical calculations at the B3LYP/aug-cc-pVDZ level of theory, we simulated the thermodynamics of decomposition reactions proceeding via substitution of the diazonium group by corresponding nucleophiles. The method applied predicted the decomposition energies of all the studied compounds fairly precise, except for 2-nitrobenzene diazonium triflate. It has been found that 4-nitrobenzene diazonium triflate has increased storage stability under normal conditions comparing to the corresponding tosylate and tetrafluoroborate. The experimental and theoretical results demonstrated that comparing to DSC/TGA, isothermal flow calorimetry more adequately reflects the energetics of the thermal decomposition of DSs and their storage stability under normal conditions.
DIBENZOOXEPIN DERIVATIVE
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Paragraph 0386, (2014/06/24)
A dibenzoxepin derivative represented by the following general formula (I) wherein Y is a hydrogen atom and the like, RA is a hydrogen atom and the like, X is the formula (b3) wherein RB is a hydrogen atom and the like, and the like,
CHIRAL PHOSPHINES FOR PALLADIUM-CATALYZED ASYMMETRIC ALPHA-ARYLATION OF ESTER ENOLATES TO PRODUCE TERTIARY STEREOCENTERS IN HIGH ENANTIOSELECTIVITY
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Paragraph 00164-00165, (2013/03/26)
The disclosure provides new and improved methods for the Pd-catalyzed asymmetric α-arylation of ester compounds, which produce the corresponding α-aryl moiety in high enantioselectivity (generally >90% ee). The present methods utilize a palladium catalyst supported by new (R)-H8-BINOL-derived monophosphine ligands. The method is applicable to a wide variety of aryl triflate substrates having variations in both electronic and steric properties. These aryl triflate substrates react with various α-alkyl (Z)- and/or (E)-0-trimethylsilyl ketene acetals in the presence of a Pd catalyst, (R)-H8-BINOL-derived monophosphine ligand, and a mild activator, for example, LiOAC, to provide the asymmetric α-arylation of ester compounds in high ee.
Intermolecular mizoroki-heck reaction of aliphatic olefins with high selectivity for substitution at the internal position
Qin, Liena,Ren, Xinfeng,Lu, Yunpeng,Li, Yongxin,Zhou, Jianrong
supporting information; experimental part, p. 5915 - 5919 (2012/07/30)
New ligand for old reaction: The title reaction of aryltriflates with aliphatic olefins leads to substitution at the internal position with high selectivity. The ratio of the desired isomer (shown in the scheme) to the sum of all other isomers is generall
Regioselectivity switch achieved in the palladium catalyzed α-arylation of enones by employing the modified Kuwajima-Urabe conditions
Kale, Ajit Prabhakar,Pawar, Govind Goroba,Kapur, Manmohan
supporting information; experimental part, p. 1808 - 1811 (2012/06/18)
A new regioselective approach to the synthesis of α-aryl enones is reported. This represents an important application of the Kuwajima-Urabe protocol toward the synthesis of this simple albeit complex functional array. Several α-aryl enones were synthesized by the palladium catalyzed arylation of triethylsilylenol ethers of enones with high regioselectivity and broad scope, utilizing sterically encumbered electron-rich phosphine ligands to drive the reaction.
Synthesis of enantiomerically enriched 3-amino-2-oxindoles through a palladium-mediated asymmetric intramolecular arylation of α-ketimino amides
Tolstoy, Paeivi,Lee, Samantha X. Y.,Sparr, Christof,Ley, Steven V.
supporting information, p. 4810 - 4813,4 (2012/12/12)
A highly efficient and enantioselective synthesis of 3-amino-2-oxindoles through a palladium-catalyzed asymmetric intramolecular arylation of R-ketimino amides using (R)-DiFluorPhos as the coordinating ligand is reported. This report constitutes the first
Synthesis of enantiomerically enriched 3-amino-2-oxindoles through a palladium-mediated asymmetric intramolecular arylation of α-ketimino amides
Tolstoy, P?ivi,Lee, Samantha X.Y.,Sparr, Christof,Ley, Steven V.
supporting information, p. 4810 - 4813 (2013/01/15)
A highly efficient and enantioselective synthesis of 3-amino-2-oxindoles through a palladium-catalyzed asymmetric intramolecular arylation of R-ketimino amides using (R)-DiFluorPhos as the coordinating ligand is reported. This report constitutes the first
Palladium-catalyzed desulfitative arylation by C-O bond cleavage of aryl triflates with sodium arylsulfinates
Zhou, Chao,Liu, Qingjiang,Li, Yaming,Zhang, Rong,Fu, Xinmei,Duan, Chunying
, p. 10468 - 10472 (2013/01/15)
An efficient Pd-catalyzed desulfitative coupling reaction of sodium arylsulfinates as arylation reagents by C-O bond cleavage of aryl triflates was developed. With only 2 mol % of Pd(OAc)2 as catalyst and XPhos as ligand, the reaction proceeded well for a range of substrates.
An enantioselective, intermolecular α-arylation of ester enolates to form tertiary stereocenters
Huang, Zhiyan,Liu, Zheng,Zhou, Jianrong
supporting information; experimental part, p. 15882 - 15885 (2011/11/13)
In transition-metal catalyzed, asymmetric α-arylation of carbonyl compounds, formation of tertiary centers with high enantioselectivity is a longstanding problem, due to easy enolization of the monoarylation products. Herein, we report such examples using a palladium catalyst supported by a new, (R)-H8-BINOL-derived monophosphine. Silyl ketene acetals, together with a weakly basic activator, were used as equivalents of ester anions, and they reacted smoothly with aryl triflates in excellent enantiomeric excess (ee). The usefulness of the reaction was demonstrated in a gram-scale synthesis of (S)-Naproxen in 92% ee.
