13395-85-2Relevant 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.
Toward a Catalytic Atroposelective Synthesis of Diaryl Ethers Through C(sp 2)-H Alkylation with Nitroalkanes
Dinh, Andrew N.,Noorbehesht, Ryan R.,Toenjes, Sean T.,Jackson, Amy C.,Saputra, Mirza A.,Maddox, Sean M.,Gustafson, Jeffrey L.
supporting information, p. 2155 - 2160 (2018/09/29)
We report studies toward a small-molecule-catalytic approach to access atropisomeric diaryl ethers that proceeds through a C(sp 2)-H alkylation using nitroalkanes as the alkyl source. A quaternary ammonium salt derived from quinine, containing
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.
POLYESTER STEREOCOMPLEXES, COMPOSITIONS COMPRISING SAME, AND METHODS OF MAKING AND USING SAME
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Paragraph 0100, (2016/02/29)
Compositions comprising stereocomplexes of enantiomeric polymer chains having individual repeat units formed from the reaction of an epoxide and cyclic anhydride. The compositions can be made by mixing two types of enantiomeric polymer chains having opposite absolute stereochemistry. The compositions can be used in applications such as biomedical applications and drug delivery applications.
Development of Highly Active and Regioselective Catalysts for the Copolymerization of Epoxides with Cyclic Anhydrides: An Unanticipated Effect of Electronic Variation
Diciccio, Angela M.,Longo, Julie M.,Rodríguez-Calero, Gabriel G.,Coates, Geoffrey W.
supporting information, p. 7107 - 7113 (2016/07/06)
Recent developments in polyester synthesis have established several systems based on zinc, chromium, cobalt, and aluminum catalysts for the ring-opening alternating copolymerization of epoxides with cyclic anhydrides. However, to date, regioselective proc
2,2,6,6-Tetramethylpiperidine-catalyzed, ortho-selective chlorination of phenols by sulfuryl chloride
Saper, Noam I.,Snider, Barry B.
, p. 809 - 813 (2014/04/03)
2,2,6,6-Tetramethylpiperidine (TMP)-catalyzed (1- 10%) chlorinations of phenols by SO2Cl2 in aromatic solvents are more ortho selective than with primary and less hindered secondary amine catalysts. Ortho-selective chlorination is successful even with electron deficient phenols such as 2-hydroxybenzaldehyde and 2'- hydroxyacetophenone. Notably, ortho selectivity increases with the reaction temperature. On the other hand, tetraalkylammonium chloride-catalyzed chlorinations are moderately para selective.
Poly(propylene succinate): A new polymer stereocomplex
Longo, Julie M.,Diciccio, Angela M.,Coates, Geoffrey W.
supporting information, p. 15897 - 15900 (2015/02/19)
Herein we show the formation of a polymer stereocomplex by mixing isotactic, regioregular chains of poly(propylene succinate) synthesized via the copolymerization of cyclic anhydrides and epoxides. The stereocomplex exhibits significantly improved thermal
PYRROLO CARBOXAMIDES AS MODULATORS OF ORPHAN NUCLEAR RECEPTOR RAR-RELATED ORPHAN RECEPTOR-GAMMA (ROR?, NR1F3) ACTIVITY AND FOR THE TREATMENT OF CHRONIC INFLAMMATORY AND AUTOIMMUNE DISEASES
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Page/Page column 77, (2013/06/27)
The invention provides modulators for the orphan nuclear receptor ROR? and methods for treating ROR? mediated diseases by administrating these novel ROR? modulators to a human or a mammal in need thereof. Specifically, the present invention provides pyrrolo carboxamide compounds of Formula (1) and the enantiomers, diastereomers, N-oxides, tautomers, solvates and pharmaceutically acceptable salts thereof.
Synthesis of differently substituted tacn-based ligands: Towards the control of solubility and electronic and steric properties of uranium coordination complexes
Nizovtsev, Alexey V.,Scheurer, Andreas,Kosog, Boris,Heinemann, Frank W.,Meyer, Karsten
, p. 2538 - 2548 (2013/07/11)
Starting from phenols R1,R2ArOH (5) and the anisole derivative 3,5-di-tert-butyl-2-methoxybenzyl bromide (13), a series of new tacn-based ligands (R1,R2ArOR3)3tacn (2) have been synthesized with substituents of
HETEROCYCLIC COMPOUND
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Page/Page column 58-59, (2010/07/08)
The present invention relates to wherein each symbol is as defined in the specification. The compound of the present invention has a superior RBP4-lowering action, and is useful as a medicament for the prophylaxis or treatment of disease and condition mediated by increased RBP4.
