94064-81-0

Upstream product

• 90-14-2 1-Iodonaphthalene 
• 585-79-5 m-nitrobromobenzene 
• 85-46-1 1-Naphthalenesulfonyl chloride 
• 13331-27-6 m-nitrobenzene boronic acid 
• 90-11-9 1-Bromonaphthalene 
• 645-00-1 m-iodonitrobenzene 
• 90-13-1 1-Chloronaphthalene 
• 13922-41-3 1-Naphthylboronic acid 
• 99-09-2 3-nitro-aniline 
• 68716-48-3 4,4,5,5-tetramethyl-2-(3-nitrophenyl)-1,3,2-dioxaborolane 
• 121-92-6 3-nitrobenzoic acid 
• 135-19-3 β-naphthol 
• 91-20-3 naphthalene 
• 79048-31-0 tributyl(3-nitrophenyl)stannane 

Downstream Products

• 728919-25-3 3-(naphthalen-1-yl)aniline 

Relevant academic research and scientific papers

One-pot Suzuki coupling of aromatic amines via visible light photocatalyzed metal free borylation using t-BuONO at room temperature

A convenient and efficient metal free borylation of aromatic amines has been achieved using tertiary butyl nitrite and B2Pin2 (bis(pinacolato)diborane) under irradiation with blue LED light at room temperature. This protocol has been successfully extended to subsequent Suzuki coupling in the same pot. Thus a series of functionalized aryl boronates and biaryls are obtained in high yields in a shorter reaction period starting from relatively cheap aryl amines in one-pot avoiding isolation of potentially unstable and hazardous intermediates.

Catalytic Decarboxylative Cross-Coupling of Aryl Chlorides and Benzoates without Activating ortho Substituents

The restriction of decarboxylative cross-coupling reactions to ortho-substituted or heterocyclic carboxylate substrates was overcome by holistic optimization of a bimetallic Cu/Pd catalyst system. The combination of a CuI/Me4phen decarboxylation catalyst and a [(MeCN)4Pd](OTf)2/XPhos cross-coupling catalyst enables the synthesis of biaryls from inexpensive aryl chlorides and potassium benzoates regardless of their substitution pattern. Lifting the restriction: A combination of a CuI/Me4phen decarboxylation catalyst and a [(MeCN)4Pd](OTf)2/XPhos cross-coupling catalyst enables the synthesis of biaryls from inexpensive aryl chlorides and potassium benzoates regardless of their substitution pattern (see scheme; FG=functional group). This approach lifts the restriction of decarboxylative cross-coupling reactions to ortho-substituted or heterocyclic carboxylate substrates.

Decarboxylative cross-coupling of mesylates catalyzed by copper/palladium systems with customized imidazolyl phosphine ligands

The activation of the inert C-O bonds in mesylates through the use of a new class of imidazolyl phosphines allows the decarboxylative coupling of aryl mesylates as well as polysubstituted alkenyl mesylates. Variation of the ligands leads to two complementary methods providing the corresponding biaryls and polysubstituted olefins in good yields. Copyright

Asymmetric anthracene-based blue host materials: Synthesis and electroluminescence properties of 9-(2-naphthyl)-10-arylanthracenes

A series of bulky aryl-substituted asymmetric anthracene blue host materials, 9-(2-naphthyl)-10-(3-(1-naphthyl)phenyl)anthracene, where phenyl was varied from H (5a), Me (5b), Ph (5e), and 1-Naph (5f) at the 6-position and Me (5c) at the 2-position, was s

Rational exploration of N-Heterocyclic carbene (NHC) palladacycle diversity: A highly active and versatile precatalyst for suzuki-miyaura coupling reactions of deactivated aryl and alkyl substrates

As less attention has been focussed on the design of highly efficient palladium precatalysts to ensure the smooth formation of the active catalyst for metal-mediated cross coupling reactions, we herein demonstrate that combining the bulky N-heterocyclic carbene (NHC) 1,3-bis(2,6-diisopropylphenyl)imidazol-2- ylidene (IPr) with cyclopalladated acetanilide as the optimal palladium precatalyst leads to superior catalytic activity compared with the state-of-the-art NHC-Pd catalysts. The complex was discovered through the evaluation of a small, rationally designed library of NHC-palladacycles prepared by a novel, practical and atom-economic method, the direct reaction of IPrHCl with palladacycle acetate dimers.

Preparation of unsymmetrical biaryls by pd(II)-catalyzed cross-coupling of aryl iodides

The Ullmann homo-and cross-couplings of aryl iodides are carried out to afford symmetrical and unsymmetrical biaryls in moderate to good yields in a catalytic system of Pd(OAc)2/K2CO3/MeCOEt. The high selectivity of unsymmetrical biaryl products in cross-couplings mainly depends on the reactivity difference between two iodoarene substrates and their employed ratios.

Phosphine-free palladium(II)-catalyzed arylation of naphthalene and benzene with aryl iodides

(Chemical Equation Presented) A phosphine-free arylation of naphthalene and benzene with aryl iodides to give biaryls in moderate to good yields is carried out in the presence of catalytic Pd(OAc)2 and stoichiometric CF 3CO2 Ag in TFE or/and TFA.

Microwave-assisted Suzuki coupling reactions with an encapsulated palladium catalyst for batch and continuous-flow transformations

This article describes the design, optimisation and development of a Suzuki cross-coupling protocol mediated by an efficient palladium-en-capsulated catalyst (Pd EnCat) under microwave irradiation. The methodology has been used in both batch mode for classical library preparation and in continuous-flow applications furnishing multigram quantities of material. Described is a method that uses direct focused microwave heating whilst applying an external cooling source. This enables a lower than normal bulk temperature to be maintained throughout the reaction period leading to significant improvements in the overall yield and purity of the reaction products. Additional aspects of this novel heating protocol are discussed in relation to the prolonged lifetime and enhanced reactivity of the immobilised catalyst system.

Palladium-Catalyzed Suzuki - Miyaura Cross-Couplings of Sulfonyl Chlorides and Boronic Acids

(Equation presented) Arene-, arylmethane, and alk-2-ene-1-sulfonyl chlorides undergo Suzuki - Miyaura cross-coupling with arene-, heteroarene-, and alkeneboronic acids in THF at reflux. The reactivity order is Arl > ArSO2Cl > ArBr ? ArCl.

Palladium-Catalyzed Stille Cross-Couplings of Sulfonyl Chlorides and Organostannanes

Arene and phenylmethanesulfonyl chlorides can be cross-coupled with aryl, heteroaryl, and alkenylstannanes with desulfitation in the presence of 10 mol % CuBr·Me2S, 1.5 mol % Pd2dba3, and 5 mol % tri-2-furylphosphine in tetrahydrofuran or toluene under reflux. This extension of the Stille cross-coupling reaction realizes a new and economical method for the generation of C?C bonds. The palladium-catalyzed carbonylative Stille cross-coupling reactions of arenesulfonyl chlorides and organostannanes in the presence of CO (60 bar) at 110 °C in toluene generate the corresponding ketones. Arenesulfonyl chlorides are more reactive than aryl chlorides and aryl bromides in their Stille cross-coupling with organostannanes but less reactive than aryl iodides. The new methods disclosed for the generation of C?C bonds open new possibilities for medicinal chemistry and material sciences. Copyright