365426-93-3

Upstream product

• 626-02-8 3-Iodophenol 
• 128796-39-4 4-trifluoromethylphenylboronic acid 
• 122924-26-9 3--2-cyclohexen-1-one 
• 455-13-0 4-Iodobenzotrifluoride 
• 69-72-7 salicylic acid 
• 871231-45-7 potassium (3-hydroxyphenyl)trifluoroborate 
• 109541-76-6 tris(4-(trifluoromethyl)phenyl)bismuthane 
• 591-20-8 3-Bromophenol 
• 177171-16-3 3-(trimethylsilyl)phenylboronic acid 
• 90-02-8 salicylaldehyde 
• 930-68-7 cyclohexenone 
• 108-43-0 3-monochlorophenol 
• 98-56-6 4-chlorobenzotrifluoride 
• 122902-06-1 3-<4-(Trifluoromethyl)phenyl>cyclohexanone 

Relevant academic research and scientific papers

Electrochemical Synthesis of Biaryls via Oxidative Intramolecular Coupling of Tetra(hetero)arylborates

We report herein versatile, transition metal-free and additive-free (hetero)aryl-aryl coupling reactions promoted by the oxidative electrocoupling of unsymmetrical tetra(hetero)arylborates (TABs) prepared from ligand-exchange reactions on potassium trifluoroarylborates. Exploiting the power of electrochemical oxidations, this method complements the existing organoboron toolbox. We demonstrate the broad scope, scalability, and robustness of this unconventional catalyst-free transformation, leading to functionalized biaryls and ultimately furnishing drug-like small molecules, as well as late stage derivatization of natural compounds. In addition, the observed selectivity of the oxidative coupling reaction is related to the electronic structure of the TABs through quantum-chemical calculations and experimental investigations.

Pd-catalyzed protecting-group-free cross-couplings of iodophenols with atom-economic triarylbismuth reagents

An efficient protocol for the protecting-group-free synthesis of unsymmetrical hydroxybiaryls via the Pd-catalyzed cross-couplings of unprotected iodophenols with triarylbismuth reagents is described. The presented protocols exhibits good to high yields of hydroxybiaryls.

Catalyst shuttling enabled by a thermoresponsive polymeric ligand: Facilitating efficient cross-couplings with continuously recyclable ppm levels of palladium

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.

Light-Induced Gold-Catalyzed Hiyama Arylation: A Coupling Access to Biarylboronates

Organoboron compounds are versatile synthetic building blocks. We herein report a new strategy, a photochemical gold-catalyzed chemo-selective Hiyama arylation of B,Si bifunctionalized reagents with diazonium salts, which is orthogonal to common strategies and therefore a unique tool for synthesis of valuable biarylboronates. With this new methodology a wide array of diversely functionalized sp2- and sp3-hybridized biarylboronates were obtained. Notably, the synergism of gold catalysis with copper catalysis or palladium catalysis, allows for one-pot iterative C?X (heteroatom) and C?C couplings for the rapid assembly of several simple fragments to relatively complex molecules. Mechanistic studies indicated that photosensitizer-free conditions were superior to gold/Ru(bpy)3Cl2 dual catalysis.

3-Hydroxypyrimidine-2,4-diones as Selective Active Site Inhibitors of HIV Reverse Transcriptase-Associated RNase H: Design, Synthesis, and Biochemical Evaluations

Human immunodeficiency virus (HIV) reverse transcriptase (RT) associated ribonuclease H (RNase H) remains an unvalidated antiviral target. A major challenge of specifically targeting HIV RNase H arises from the general lack of selectivity over RT polymerase (pol) and integrase (IN) strand transfer (ST) inhibitions. We report herein the synthesis and biochemical evaluations of three novel 3-hydroxypyrimidine-2,4-dione (HPD) subtypes carefully designed to achieve selective RNase H inhibition. Biochemical studies showed the two subtypes with an N-1 methyl group (9 and 10) inhibited RNase H in low micromolar range without siginificantly inhibiting RT polymerase, whereas the N-1 unsubstituted subtype 11 inhibited RNase H in submicromolar range and RT polymerase in low micromolar range. Subtype 11 also exhibited substantially reduced inhibition in the HIV-1 INST assay and no significant cytotoxicity in the cell viability assay, suggesting that it may be amenable to further structure-activity relationship (SAR) for identifying RNase H inhibitors with antiviral activity.

A Domino Oxidation/Arylation/Protodecarboxylation Reaction of Salicylaldehydes: Expanded Access to meta-Arylphenols

A method that allows salicylaldehydes to be efficiently transformed into meta-arylated phenol derivatives through a cascade oxidation/arylation/protodecarboxylation sequence is presented. We demonstrate that the aldehyde functional group can be used as a convenient removable directing group to control site selectivity in C-H activation. Aldehydes are easily introduced into the starting materials and the group is readily cleaved after the C-H functionalization event.

THROMBOXANE RECEPTOR ANTAGONISTS

The invention relates to novel chemical entities that act as thromboxane (TX) A2 receptor, or T prostanoid receptor (TP), antagonists and to their use in the treatment of human diseases in which thromboxane (TX) A and of all other agents that act as incid

Continuous-Flow Synthesis of meta-Substituted Phenol Derivatives

Two complementary microreactor technologies were developed for the study of biphasic gas-liquid reactions and preparation of meta-substituted phenol derivatives. The first capillary microreactor, composed of a T-junction and simple capillary, enabled oxidative Heck/dehydrogenation on a microgram scale with a shortened reaction time; the total sequence time for oxidative Heck/dehydrogenation reactions was optimized from 2160 min in a traditional batch system to 130 min in the microchemical system. The second tube-in-tube microreactor, composed of a gas-permeable inner tube and gas-nonpermeable outer tube, successfully performed a gram-scale synthesis under the optimized safety and economic conditions which were established from the first microgram-scale study. The two microreactors have great potential for exploring reactions involving gaseous and liquid reagents.

Salicylic acids as readily available starting materials for the synthesis of meta-substituted biaryls

Salicylic acids are shown to be readily available and versatile starting materials that easily undergo a tandem arylation-protodecarboxylation process under Pd-catalysis. The corresponding meta-arylphenols can subsequently be easily transformed into a variety of meta-functionalized biaryls, highlighting the versatility of this approach to access this structural motif.

Salicylic acids as readily available starting materials for the synthesis of meta-substituted biaryls

Salicylic acids are shown to be readily available and versatile starting materials that easily undergo a tandem arylation-protodecarboxylation process under Pd-catalysis. The corresponding meta-arylphenols can subsequently be easily transformed into a var