594823-69-5

Usage

Uses

Used in Pharmaceutical Industry:
5-NAPHTHALEN-1-YL-BENZO[1,3]DIOXOLE is used as a building block for the development of pharmaceuticals due to its unique chemical structure, which can be incorporated into the design of new drugs with potential therapeutic applications.
Used in Organic Synthesis:
In the field of organic synthesis, 5-NAPHTHALEN-1-YL-BENZO[1,3]DIOXOLE is employed as an intermediate compound for the creation of a variety of organic molecules. Its structural features make it a valuable component in the synthesis of complex organic compounds with diverse applications.

Upstream product

• 90-11-9 1-Bromonaphthalene 
• 109586-40-5 1,3-dihydroisobenzofuran-5-yl trifluoromethanesulfonate 
• 703-55-9 1-naphthylmagnesiumbromide 
• 1351445-39-0 N,N,N-trimethyl-1-naphthalenaminium trifluoromethanesulfonate 
• 94839-07-3 3,4-(methylenedioxy)-benzeneboronic acid 
• 86-56-6 N,N-dimethyl-1-naphthalenamine 
• 7228-38-8 5-chloro-1,3-benzodioxole 

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.

Pd-Catalyzed Suzuki-Miyaura and Hiyama-Denmark Couplings of Aryl Sulfamates

Using a recently discovered precatalyst, the first Pd-catalyzed Suzuki-Miyaura reactions using aryl sulfamates that occur at room temperature are reported. In complementary work, it is demonstrated that a related precatalyst can facilitate the coupling of aryl silanolates, which are less toxic and reactive nucleophiles than boronic acids with aryl chlorides. By combining our results using modern electrophiles and nucleophiles, the first Hiyama-Denmark reactions using aryl sulfamates are reported.

Nickel or Iron Catalysed Carbon-Carbon Coupling Reaction of Arylenes, Alkenes and Alkines

Organozinc compounds of the type R1—Ar1—ZnY (1) can be reacted with different functionalized aryl halides R2—Ar2—X (2) in the presence of catalytic amounts of Ni or Fe in a polar solvent or solvent mixture to form polyfunctional biaryles of the type R1—Ar1—Ar2—R2 (3). Organozinc compounds of the type (1) can be represented by the transmetallation reaction of functionalized aryl magnesium halides or lithium aryl compounds with e.g. ZnBr2.

Efficient cross-coupling of functionalized arylzinc halides catalyzed by a nickel chloride-diethyl phosphite system

(Chemical Equation Presented) The combination of diethyl phosphite and DMAP as ligands for nickel in an 8:1 THF-N-ethylpyrrolidinone (NEP) mixture allows a very efficient cross-coupling reaction to be performed between various functionalized arylzinc halides and aryl bromides, triflates and activated chlorides. The reaction proceeds at 25°C within 1-48 h and requires only 0.05 mol % of the nickel catalyst.

5,6,7,12-Tetrahydrodibenz[c,f][1,5]azabismocines: Highly reactive and recoverable organo-bismuth reagents for cross-coupling reactions with Aryl Bromides

Hypervalent organobismuth compounds efficiently couple with aryl bromides in the presence of [Pd(PPh3)4] catalyst. Application of this protocol to a one-pot multi-coupling reaction with bromophenylboronic esters leads to the formation of up to nine bonds in good yields (see scheme).