572-52-1

Upstream product

• 7609-61-2 4-(4-fluoro-phenyl)-naphthalene-1,2-dicarboxylic acid-anhydride 
• 388-65-8 4-(4-fluorophenyl)-1,2-dihydronaphthalene 
• 529-34-0 3,4-dihydronaphthalene-1(2H)-one 
• 352-13-6 4-flourophenylmagnesium bromide 
• 90-11-9 1-Bromonaphthalene 
• 437-29-6 tris(4-fluorophenyl)bismuthane 
• 85-46-1 1-Naphthalenesulfonyl chloride 
• 17151-47-2 tributyl(4-fluorophenyl)stannane 
• 13922-41-3 1-Naphthylboronic acid 
• 460-00-4 1-Bromo-4-fluorobenzene 
• 90-15-3 α-naphthol 
• 1144-13-4 naphthalen-1-yl N,N-dimethylsulfamate 
• 1765-93-1 4-fluoroboronic acid 
• 732306-64-8 bis(4-fluorophenyl)iodonium triflate 

Downstream Products

• 1028729-05-6 4,4,5,5-tetramethyl-2-(4-(naphthalen-1-yl)phenyl)-1,3,2-dioxaborolane 
• 22871-77-8 5,5-dimethyl-2-(naphthalen-1-yl)-1,3,2-dioxaborinane 

Relevant academic research and scientific papers

C(sp2)-C(sp2) Suzuki cross-coupling of arylammonium salts catalyzed by a stable Pd–NHC complex

We have developed the Suzuki-Miyaura cross-coupling of aryl ammonium salts via C–N bond activation catalyzed by an easily prepared and bench-stable palladium-N-heterocyclic carbene complex. The reaction proceeded well under mild conditions with phenylboronic acid, pinacol ester or anhydride and provided yields of products up to 97% with good functional group compatibility. The direct arylation of arylamine can be performed by a two-step one-pot process and the protocol can be performed on the gram scale.

MeOTf-catalyzed formal [4?+?2] annulations of styrene oxides with alkynes leading to polysubstituted naphthalenes through sequential electrophilic cyclization/ring expansion

MeOTf-catalyzed formal [4 + 2] annulation of styrene oxides with alkynes to afford polysubstituted naphthalenes has been realized, which undergoes sequential electrophilic cyclization/ring expansion. A range of substrates were tolerated in the formation of naphthalene derivatives with high regioselectivity in satisfactory yields. The reaction could also be carried out on gram scale.

Nickel-Catalyzed Stille Cross Coupling of C-O Electrophiles

Aryl sulfamates, tosylates, and mesylates undergo efficient Ni-catalyzed cross coupling with diverse organostannanes in the presence of relatively unhindered alkylphosphine ligands and KF. The coupling is valuable for difficult bond constructions, such as aryl - heteroaryl, aryl - alkenyl, and aryl - alkynyl, using nontriflate phenol derivatives. A combination of experimental and computational studies implicates an unusual mechanism for transmetalation involving an 8-centered cyclic transition state. This reaction is inhibited by chloride sources due to slow transmetalation of organostannanes at a Ni(II) - chloride intermediate. These studies help to explain why prior efforts to achieve Ni-catalyzed Stille coupling of phenol derivatives were unsuccessful.

Pd/NHC-catalyzed cross-coupling reactions of nitroarenes

N-Heterocyclic carbene (NHC) ligands effective for the cross-coupling of nitroarenes were identified. A rational design of the NHC ligand structures enabled significant reduction of catalyst loadings compared with the previous system employing BrettPhos as a phosphine ligand. Experimental and theoretical studies to compare these ligands gave some insights into high activity of the newly developed NHC ligands.

Sterically hindered N-heterocyclic carbene/palladium(ii) catalyzed Suzuki-Miyaura coupling of nitrobenzenes

Palladium-catalyzed denitrative Suzuki coupling of nitroarenes using 2-aryl-5-(2,4,6-triisopropylphenyl)-2,3-imidazolylidene[1,5-a]pyridines as the ligands is described. The key to success is the use of the NHC ligands which show strong donating ability and suitable steric hindrance allowing the successful oxidative addition of Ar-NO2 bonds. Both aromatic and aliphatic boronic acids are tolerated, and a variety of biphenyls and alkylarenes were obtained in good to excellent yields.

Nickel-Catalyzed Csp2-Csp3 Bond Formation via C-F Bond Activation

A nickel-catalyzed cross coupling of aryl fluorides via C-F bond activation has been developed. The alkylation method allows selective replacement of aryl fluorides by alkyl groups and enables the synthesis of diverse and otherwise difficult to access scaffolds in good yields.

Iron-catalyzed coupling of aryl sulfamates and aryl/vinyl tosylates with aryl grignards

The iron-catalyzed coupling of aryl sulfamates and tosylates with aryl Grignard reagents is reported for the first time. The methodology employs air-stable, low-cost FeF3·3H2O and the N-heterocyclic carbene ligand IPr·HCl as the preligand to form a long-lived catalyst upon treatment with aryl Grignards. The reaction provides a range of cross-coupled products in good-to-excellent yields. In contrast to previous reports with aryl chlorides, these reactions proceed with low levels of Grignard homocoupling regardless of the iron source.

Palladium-catalyzed Suzuki-Miyaura coupling of aryl sulfamates with arylboronic acids

Readily available NHC-Pd(ii)-Mp complexes 2 showed efficient catalytic activity toward the Suzuki-Miyaura coupling of aryl sulfamates with arylboronic acids or potassium phenyltrifluoroborate, giving the expected coupling products in good to high yields.

Synthesis of naphthalene derivatives through inexpensive BF 3·Et2O-catalyzed annulation reaction of arylacetaldehydes with arylalkynes

An inexpensive BF3·Et2O-catalyzed annulation reaction of arylacetaldehydes with arylalkynes has been developed. Various substituted phenylacetaldehydes and phenylacetylenes can undergo this reaction, producing corresponding α-aryl su

Base- and metal-free C-H direct arylations of naphthalene and other unbiased arenes with diaryliodonium salts

A novel metal-free direct arylation of unbiased arenes with diaryliodonium triflates in a process where the use of solvents and additives is not required has been established.