607-12-5Relevant academic research and scientific papers
Catalyst-Controlled Regioselective Chlorination of Phenols and Anilines through a Lewis Basic Selenoether Catalyst
Dinh, Andrew N.,Maddox, Sean M.,Vaidya, Sagar D.,Saputra, Mirza A.,Nalbandian, Christopher J.,Gustafson, Jeffrey L.
, p. 13895 - 13905 (2020/11/03)
We report a highly efficient ortho-selective electrophilic chlorination of phenols utilizing a Lewis basic selenoether catalyst. The selenoether catalyst resulted in comparable selectivities to our previously reported bis-thiourea ortho-selective catalyst, with a catalyst loading as low as 1%. The new catalytic system also allowed us to extend this chemistry to obtain excellent ortho-selectivities for unprotected anilines. The selectivities of this reaction are up to >20:1 ortho/para, while the innate selectivities for phenols and anilines are approximately 1:4 ortho/para. A series of preliminary studies revealed that the substrates require a hydrogen-bonding moiety for selectivity.
COMPOUND AND ORGANIC LIGHT EMITTING DEVICE COMPRISING THE SAME
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Paragraph 0154-0157, (2019/11/21)
The present invention provides a compound represented by chemical formula and an organic light emitting device comprising the same. The organic light emitting device comprising the compound has excellent electrochemical and thermal stability, thereby having excellent lifespan characteristics.COPYRIGHT KIPO 2020
SHMT INHIBITORS AND USES THEREOF
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Paragraph 00235, (2018/06/30)
The present invention provides compounds, compositions thereof, and methods of using the same.
The Catalyst-Controlled Regiodivergent Chlorination of Phenols
Maddox, Sean M.,Dinh, Andrew N.,Armenta, Felipe,Um, Joann,Gustafson, Jeffrey L.
supporting information, p. 5476 - 5479 (2016/11/17)
Different catalysts are demonstrated to overcome or augment a substrate's innate regioselectivity. Nagasawa's bis-thiourea catalyst was found to overcome the innate para-selectivity of electrophilic phenol chlorination, yielding ortho-chlorinated phenols that are not readily obtainable via canonical electrophilic chlorinations. Conversely, a phosphine sulfide derived from 2,2′-Bis(diphenylphosphino)-1,1′-binaphthyl (BINAP) was found to enhance the innate para-preference of phenol chlorination.
Condensed-cyclic compound and organic light emitting diode comprising the same
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Paragraph 0401; 0404-0405, (2016/11/24)
Disclosed are a condensed-ring compound and an organic light-emitting device comprising the same. The condensed-ring compound is represented by chemical formula 1. The organic light-emitting device comprising the condensed-ring compound can have low driving voltage, high efficiency, high brightness, and long durability.COPYRIGHT KIPO 2016
Synthesis of 2,2′-biphenols through direct C(sp2)-H hydroxylation of [1,1′-biphenyl]-2-ols
Duan, Shitao,Xu, Yuanshuang,Zhang, Xinying,Fan, Xuesen
supporting information, p. 10529 - 10532 (2016/09/02)
A novel synthesis of diversely substituted 2,2′-biphenols through Pd(ii)-catalyzed, tBuOOH-oxidized, and hydroxyl-directed C(sp2)-H hydroxylation of [1,1′-biphenyl]-2-ols has been developed. Notably, this finding is distinct from previous reports in which [1,1′-biphenyl]-2-ols underwent an intramolecular C-H activation and C-O bond formation to afford dibenzofurans under the promotion of Pd(ii) but in the absence of tBuOOH.
P-directed borylation of phenols
Cazorla, Clément,De Vries, Timothy S.,Vedejs, Edwin
, p. 984 - 987 (2013/04/10)
Internal borylation occurs upon activation of aryl di-isopropylphosphinite boranes with HNTf2 to give heterocyclic intermediates that can be reductively quenched to afford 6 or treated with KHF2 to give the phenolic potassium aryl trifluoroborate salts 10. The latter salts are useful for Pd-catalyzed coupling with aryl iodides under Molander conditions, provided that precautions are taken to remove the KNTf2 byproduct from the preceding KHF2 step.
Oxidative cyclization of 2-arylphenols to dibenzofurans under Pd(II)/peroxybenzoate catalysis
Wei, Ye,Yoshikai, Naohiko
supporting information; scheme or table, p. 5504 - 5507 (2011/12/05)
2-Arylphenols undergo intramolecular C-H bond activation/C-O bond formation to afford dibenzofuran derivatives under palladium catalysis in the presence of tert-butyl peroxybenzoate as an oxidant. Kinetic isotope effect experiments indicated that C-H bond cleavage is the rate-limiting step of the reaction.
Well-defined air-stable palladium HASPO complexes for efficient Kumada-Corriu cross-couplings of (Hetero)aryl or alkenyl tosylates
Ackermann, Lutz,Kapdi, Anant R.,Fenner, Sabine,Kornhaab, Christoph,Schulzke, Carola
supporting information; experimental part, p. 2965 - 2971 (2011/05/05)
Palladium complexes of representative heteroatom-substituted secondary phosphine oxide (HASPO) preligands were synthesized and fully characterized, including X-ray crystal structure analysis. Importantly, these well-defined complexes served as highly efficient catalysts for Kumada-Corriu cross-coupling reactions of aryl, alkenyl, and even heteroaryl tosylates. Particularly, an air-stable catalyst derived from inexpensive PinP(O)H displayed a remarkably high catalytic efficacy, which resulted in cross-couplings at low catalyst loadings under exceedingly mild reaction conditions with ample scope.
Dichloro-bis(aminophosphine) complexes of palladium: Highly convenient, reliable and extremely active suzuki-miyaura catalysts with excellent functional group tolerance
Bolliger, Jeanne L.,Frech, Christian M.
experimental part, p. 4075 - 4081 (2010/08/05)
Dichloro-bis(aminophosphine) complexes are stable depot forms of palladium nanoparticles and have proved to be excellent SuzukiMiyaura catalysts. Simple modifications of the ligand (and/or the addition of water to the reaction mixture) have allowed their formation to be controlled. Dichlorobis[1- (dicyclohexylphosphany1)piperidine]palladium (3), the most active catalyst of the investigated systems, is a highly convenient, reliable, and extremely active Suzuki catalyst with excellent functional group tolerance that enables the quantitative coupling of a wide variety of activated, nonactivated, and deactivated and/or sterically hindered functionalized and heterocyclic aryl and benzyl bromides with only a slight excess (1.1-1.2 equiv) of arylboronic acid at 80°C in the presence of 0.2 mol % of the catalyst in technical grade toluene in flasks open to the air. Conversions of >95% were generally achieved within only a few minutes. The reaction protocol presented herein is universally applicable. Side-products have only rarely been detected. The catalytic activities of the aminophosphine-based systems were found to be dramatically improved compared with their phosphine analogue as a result of significantly faster palladium nanoparticle formation. The decomposition products of the catalysts are dicyclohexylphosphinate, cyclohexylphosphonate, and phosphate, which can easily be separated from the coupling products, a great advantage when compared with non-water-soluble phosphine-based systems.
