69135-05-3

Upstream product

• 109-04-6 2-bromo-pyridine 
• 14221-01-3 tetrakis(triphenylphosphine) palladium⁽⁰⁾ 
• 2156-04-9 4-Vinylphenylboronic acid 
• 87199-17-5 4-formylphenylboronic acid, 
• 878376-35-3 pyridine-2-sulfonyl fluoride 
• 127406-56-8 4-(2'-pyridyl)benzaldehyde 
• 19493-09-5 Methylenetriphenylphosphorane 
• 109-09-1 2-chloropyridine 
• 802-03-9 tris(4-vinylphenyl)bismuthine 
• 5029-67-4 2-iodopyridine 
• 694-59-7 pyridine N-oxide 
• 676593-23-0 5,5-dimethyl-2-(4-ethenylphenyl)-1,3,2-dioxaborinane 
• 1779-49-3 Methyltriphenylphosphonium bromide 

Downstream Products

• 1190991-76-4 2-(pyridin-2-yl)-5-vinylbenzonitrile 
• 1262659-63-1 2-(pyridin-2-yl)-5-vinylbenzoic acid methyl ester 
• 1613027-76-1 tert-butyl [2-(pyridin-2-yl)-5-vinylphenyl]carbamate 
• 1607824-45-2 2-(2-(pyridin-2-yl)-5-vinylphenyl)isoindoline-1,3-dione 

Relevant academic research and scientific papers

Iridium luminophore complexes for unimolecular oxygen sensors

In this study, a series of novel luminescent cyclometalated Ir(III) complexes has been synthesized and evaluated for use in unimolecular oxygen-sensing materials. The complexes Ir(C6)2(vacac), 1, Ir(ppy)2-(vacac), 2, fac-Ir(ppy)2(vppy), 3, and mer-Ir(ppy)2(vppy), 4, where C6 = Coumarin 6, vacac = allylaceto-acetate, ppy = 2-phenylpyridine, and vppy = 2-(4-vinylphenyl) pyridine, all have pendent vinyl or allyl groups for polymer attachment via the hydrosilation reaction. These luminophore complexes were characterized by NMR, absorption, and emission spectroscopy, luminescence lifetime and quantum yield measurements, elemental analysis, and cyclic voltammetry. Complex 1 was structurally characterized using X-ray crystallography, and a series of 1-D (1H, 13C) and 2-D (1H-1H, 1H-13C) NMR experiments were used to resolve the solution structure of 4. Complexes 1 and 3 displayed the longest luminescence lifetimes and largest quantum efficiencies in solution (τ = 6.0 μs, φ = 0.22 for 1; τ = 0.4 μs, φ = 0.2 for 3) and, as result, are the most promising candidates for future luminescence-quenching-based oxygen-sensing studies.

‘Aggregation-Induced Emission’ Active Mono-Cyclometalated Iridium(III) Complex Mediated Efficient Vapor-Phase Detection of Dichloromethane

Selective vapor-phase detection of dichloromethane (DCM) is a challenge, it being a well-known hazardous volatile organic solvent in trace amounts. With this in mind, we have developed an ‘Aggregation-induced Emission’ (AIE) active mono-cyclometalated iri

Desulfonative Suzuki–Miyaura Coupling of Sulfonyl Fluorides

Sulfonyl fluorides have emerged as powerful “click” electrophiles to access sulfonylated derivatives. Yet, they are relatively inert towards C?C bond forming transformations, notably under transition-metal catalysis. Here, we describe conditions under which aryl sulfonyl fluorides act as electrophiles for the Pd-catalyzed Suzuki–Miyaura cross-coupling. This desulfonative cross-coupling occurs selectively in the absence of base and, unusually, even in the presence of strong acids. Divergent one-step syntheses of two analogues of bioactive compounds showcase the expanded reactivity of sulfonyl fluorides to encompass both S?Nu and C?C bond formation. Mechanistic experiments and DFT calculations suggest oxidative addition occurs at the C?S bond followed by desulfonation to form a Pd-F intermediate that facilitates transmetalation.

Catalytic α-Selective Deuteration of Styrene Derivatives

We report an operationally simple protocol for the catalytic α-deuteration of styrenes. This process proceeds via the base-catalyzed reversible addition of methanol to styrenes in DMSO-d6 solvent. The concentration of methanol is shown to be critical for high yields and selectivities over multiple competing side reactions. The synthetic utility of α-deuterated styrenes for accessing deuterium-labeled chiral benzylic stereocenters is demonstrated.

Suzuki-Miyaura cross-coupling for efficient synthesis of aryl-substituted N-heteroarenes catalyzed by recyclable N-phenylpiperazine-Palladium(II) complex

Polystyrene supported N-phenylpiperazine-Pd(II) complex D was synthesized and characterized by various techniques, including Fourier transform infrared spectroscopy (FTIR), scanning electronmicroscopy (SEM), energy dispersive X-ray spectroscopy (EDX) and thermal analysis (TG-DTA). This heterogeneous Pd(II) complex showed high catalytic efficiency for the Suzuki-Miyaura coupling of arylboronic acids with aryl bromides, aryl chlorides to give the corresponding 2-arylpyridines and heteroarenes. The coupled products were formed in excellent yields at low catalyst loadings under mild reaction conditions. Further, this heterogeneous catalyst showed excellent recyclability and reused for four cycles with no significant decrease in its activity.

Ru-Catalyzed Regioselective Direct Hydroxymethylation of (Hetero)Arenes via C-H Activation

An efficient and direct ruthenium-catalyzed regioselective hydroxymethylation of (hetero)arenes via C-H activation with paraformaldehyde as a hydroxymethylating reagent is described. The corresponding products can be obtained in good to excellent yield. A number of aryl aldehydes can also be used in place of paraformaldehyde giving the desired alcohol products with similarly good results.

Comparative Catalytic Activity of Group 9 [CpMIII] Complexes: Cobalt-Catalyzed C-H Amidation of Arenes with Dioxazolones as Amidating Reagents

A procedure for the [CpCoIII]-catalyzed direct C-H amidation of arenes with dioxazolone has been developed. This reaction proceeds under straightforward and mild conditions with a broad range of substrates, including anilides. A comparative study on the catalytic activity of Group 9 [{CpMCl2}2] complexes revealed the unique efficiency of the cobalt catalyst. Pick of the bunch: A variety of arenes, including anilides, underwent direct C-H amidation with dioxazolones in the presence of a cobalt catalyst with a Cp? ligand under mild and straightforward reaction conditions (see scheme; Piv=pivaloyl). A comparative study of Group 9 [CpMIII] complexes revealed the unique ability of the cobalt catalyst to promote this transformation efficiently.

A monolith immobilised iridium Cp catalyst for hydrogen transfer reactions under flow conditions

An immobilised iridium hydrogen transfer catalyst has been developed for use in flow based processing by incorporation of a ligand into a porous polymeric monolithic flow reactor. The monolithic construct has been used for several redox reductions demonstrating excellent recyclability, good turnover numbers and high chemical stability giving negligible metal leaching over extended periods of use.

Cross-coupling study of iodo/chloropyridines and 2-chloroquinoline with atom-economic triarylbismuth reagents under Pd-catalysis

This study describes the palladium-catalyzed couplings of iodopyridines, chloropyridines, and chloroquinoline with atom-economic BiAr3 reagents in sub-stoichiometric loadings. Mono-arylations of iodo and chloropyridines produced arylpyridines i

Copper-catalyzed direct C-H arylation of pyridine N-oxides with arylboronic esters: One-pot synthesis of 2-arylpyridines

The first example of the copper-catalyzed direct C-H arylation of pyridine N-oxides with arylboronic esters has been developed, leading to a wide range of 2-arylpyridines in a one-pot synthesis with moderate to good yields without an additional reductant. This transformation allows for rapid access to a variety of 2-arylpyridines using an inexpensive catalytic system that would be more difficult to access with traditional methods. Thus, this method represents a simple and practical procedure to access 2-arylpyridines.