154493-59-1Relevant articles and documents
Copper-Free Click Reaction Sequence: A Chemoselective Layer-by-Layer Approach
Meinecke, Jannick,Koert, Ulrich
, p. 7609 - 7612 (2019)
An additive-free chemoselective ligation of dual clickable building blocks is demonstrated. The challenge of balancing reactivity and stability was achieved by employing a small, electron-deficient tetrazine bearing an azido group and an enol ether functionalized cyclooctyne. The chemoselective sequence of strain-promoted azide-alkyne cycloaddition (SPAAC) and inverse-electron-demand Diels-Alder (IEDDA) reaction is demonstrated with a cholic acid derived triazide as a molecular surface model for layer-by-layer synthesis.
Direct probing molecular twist and tilt in aromatic self-assembled monolayers
Ballav, Nirmalya,Schuepbach, Bjoern,Dethloff, Ole,Feulner, Peter,Terfort, Andreas,Zharnikov, Michael
, p. 15416 - 15417 (2007)
Using a nitrile tailgroup as a spectroscopic marker, both twist and tilt of the aromatic backbones in several typical aromatic SAMs on Au(111) have been directly determined in a single experiment. Whereas the exact value of the twist angle depends on the molecular architecture, it was found to be quite noticeable in all SAMs (40-50°) and close to the respective value for aromatic bulk systems (32°). Copyright
PdO hydrate as an efficient and recyclable catalyst for the Suzuki-Miyaura reaction in water/ethanol at room temperature
Amoroso, Francesco,Colussi, Sara,Del Zotto, Alessandro,Llorca, Jordi,Trovarelli, Alessandro
, p. 563 - 567 (2011)
PdO?1.4H2O 1 prepared in our laboratories, as well as commercially available palladium oxides 2-4 have been found to act as efficient catalysts for the Suzuki-Miyaura reaction in ethanol/water mixture at room temperature in air. Thus, in the presence of 1 mol% catalyst, the reaction between different aryl bromides and arylboronic acids afforded a wide range of functionalized biphenyls in quantitative yield. Catalyst 1 has shown to be the most active for all couples of substrates, and it can be recovered and recycled several times without marked loss of activity. It has been demonstrated by means of suitable tests that the true catalyst is a soluble form of palladium originated by metal leaching from the metal oxide precursor. It is worth of note that the amount of catalyst both in the solution and in the isolated organic product is about 1 ppm.
Catalyst shuttling enabled by a thermoresponsive polymeric ligand: Facilitating efficient cross-couplings with continuously recyclable ppm levels of palladium
Wang, Erfei,Chen, Mao
, p. 8331 - 8337 (2019/09/30)
A polymeric monophosphine ligand WePhos has been synthesized and complexed with palladium(ii) acetate [Pd(OAc)2] to generate a thermoresponsive pre-catalyst that can shuttle between water and organic phases, with the change being regulated by temperature. The structure of the polymeric ligand was confirmed with matrix-assisted laser desorption/ionization-time-of-flight (MALDI-TOF) mass spectrometry and size-exclusion chromatography (SEC) analysis, as well as nuclear magnetic resonance (NMR) measurements. This polymeric metal complex enables highly efficient Pd-catalyzed cross-couplings and tandem reactions using 50 to 500 ppm palladium, and this can facilitate reactions that are tolerant to a broad spectrum of (hetero)aryl substrates and functional groups, as demonstrated with 73 examples with up to 99% isolated yields. Notably, 97% Pd remained in the aqueous phase after 10 runs of catalyst recycling experiments, as determined via inductively coupled plasma-atomic emission spectrometry (ICP-AES) measurements, indicating highly efficient catalyst transfer. Furthermore, a continuous catalyst recycling approach has been successfully developed based on flow chemistry in combination with the catalyst shuttling behavior, allowing Suzuki-Miyaura couplings to be conducted at gram-scales with as little as 10 ppm Pd loading. Given the significance of transition-metal catalyzed cross-coupling and increasing interest in sustainable chemistry, this work is an important step towards the development of a responsive catalyst, in addition to having high activity, by tuning the structures of the ligands using polymer science.
Peptide nanofibers decorated with Pd nanoparticles to enhance the catalytic activity for C-C coupling reactions in aerobic conditions
Maity, Indrajit,Rasale, Dnyaneshwar B.,Das, Apurba K.
, p. 2984 - 2988 (2014/01/06)
We report the synergistic effects of peptide nanofibers decorated with Pd nanoparticles to enhance the catalytic activity for C-C coupling reactions in mild and aerobic conditions.
THIAZOLE COMPOUNDS AS ACTIVATORS OF SOLUBLE GUANYLATE CYCLASE
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Page/Page column 46, (2010/04/03)
Disclosed are compounds of formula (I) wherein R1 and R2 are independently selected from hydrogen, halo, C1-4alkyl, C1-4alkoxy, CF3 and OCF3; -Y- represents formula (IA) R3 represents hydrogen, fluoro, chloro or C1-4alkyl; R4a and R4b each independently represent hydrogen, C1-4alkyl, C1-4alkoxy, CF3 or halo; and R5 represents a group Z-X; wherein Z is absent or represents (CH2)2 or O; and X represents formula (IB) wherein: J and L both represent CH, or one of J and L represents CH and the other represents N; when both J and L represent CH, R6 represents hydrogen, halo, CF3, C1-4alkyl or C1-4alkoxy in a meta or ortho position relative to the R7 substituent and R7 represents hydrogen, halo, CF3, OCF3, C1-4alkyl, C1-4alkoxy, CH2OH, CN, CONR8R9 or CO2H; or when one of J or L represents N, R6 represents hydrogen or halo in a meta or ortho position relative to the R7 substituent and R7 represents hydrogen, halo, CF3, C1-4alkyl, C1-4alkoxy, CH2OH, CN, CONR8R9 or CO2H; and R8 and R9 are independently selected from hydrogen and C1-4alkyl; or salts thereof which activate soluble guanylate cyclase (sGC), pharmaceutical compositions containing them, their use in medicine, and processes for their preparation.
PYRIMIDINE DERIVATIVES AS ACTIVATORS OF SOLUBLE GUANYLATE CYCLASE
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Page/Page column 38, (2010/04/03)
Disclosed are compounds of formula (I) and or salts thereof which activate soluble guanylate cyclase (sGC), pharmaceutical compositions containing them, their use in the manufacture of a medicament for teating cardiovascular diseases, and processes for their preparation.
2,6-DISUBSTITUTED PYRIDINES AS SOLUBLE GUANYLATE CYCLASE ACTIVATORS
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Page/Page column 62, (2009/07/17)
Disclosed are compounds of formula (I) wherein R1 and R2 are independently selected from hydrogen, halo, CF3, C1-4alkyl and allyl; Y represents (II), (III), (IV) or (V) wherein R3 represents CF3 or C1-4alkyl; and R3a represents CF3 or C1-4alkyl.
A facile one-pot preparation of potassium hydroxyaryl- and (hydroxyalkyl)aryltrifluoroborates
Park, Young Hee,Ahn, Hong Ryul,Canturk, Belgin,Jeon, Sang Ii,Lee, Seokjoon,Kang, Heonjoong,Molander, Gary A.,Ham, Jungyeob
supporting information; scheme or table, p. 1215 - 1218 (2009/04/06)
Potassium hydroxyaryl- and (hydroxyalkyl)aryltrifluoroborates have been prepared in a simple one-pot process from the corresponding hydroxy-substituted aryl halides in 51-98% yields through an in situ protection of the free hydroxyl group with τ-BuLi. Also, we successfully performed a microwave-promoted Suzuki-Miyaura cross-coupling reaction of these substrates with aryl- and alkenyl bromides in the presence of 0.5 mol % of Pd(OAc)2 catalyst without ligands.