An Expedient Route to 9-arylmethylanthracene Derivatives via Tandem Ni-catalyzed Alkene Dicarbofunctionalization and Acid-promoted Cyclization-aromatization.

  title={An Expedient Route to 9-arylmethylanthracene Derivatives via Tandem Ni-catalyzed Alkene Dicarbofunctionalization and Acid-promoted Cyclization-aromatization.},
  author={Doleshwar Niroula and Rishi R Sapkota and Roshan K. Dhungana and Bijay Shrestha and Ramesh Giri},
  journal={Israel journal of chemistry},
  volume={60 3-4},
We report a nickel-catalyzed one pot synthesis of 9-arylmethylanthracene motifs, which find applications in medicinal and material chemistry. In this synthesis, we apply three component alkene dicarbofunctionalization of 2-vinylaldimines with aryl iodides and arylzinc reagent to generate a 1,1,2-diarylethyl scaffold, which then undergoes an acidpromoted cyclization followed by aromatization to furnish 9-arylmethylanthracene cores. With the new method, a number of differently-substituted 9… 
2 Citations
Nickel-Catalyzed Dicarbofunctionalization of Alkenes.
Great opportunities exist for the development of three-component difunctionalization reactions with broad substrate scopes and tunable chemo-, regio-, and stereoselectivities.
Transition Metal (Ni, Cu, Pd)-Catalyzed Alkene Dicarbofunctionalization Reactions.
Examples of alkene dicarbofunctionalization reactions demonstrate that Cu and Ni catalysts could enable cyclization/coupling of alkenylzinc reagents, alkyl halide, and aryl halides to afford complex carbo- and heterocycles.


Copper-Catalyzed Dicarbofunctionalization of Unactivated Olefins by Tandem Cyclization/Cross-Coupling.
A strategy that difunctionalizes unactivated olefins in 1,2-positions with two carbon-based entities and a variety of (arylmethyl)carbo- and heterocycles (N, O) can be synthesized with this new method.
Ni-Catalyzed Regioselective 1,2-Dicarbofunctionalization of Olefins by Intercepting Heck Intermediates as Imine-Stabilized Transient Metallacycles.
This approach utilizes a readily removable imine as a coordinating group that plays a dual role of intercepting oxidative addition species derived from aryl halides and triflates to promote Heck carbometalation and stabilizing the Heck C(sp3)-NiX intermediates as transient metallacycles to suppress β-hydride elimination and facilitate transmetalation/reductive elimination steps.
Enantioselective 1,2-Difunctionalization of Dienes Enabled by Chiral Palladium Complex-Catalyzed Cascade Arylation/Allylic Alkylation Reaction.
A Pd-catalyzed highly enantioselective three-component coupling of 1,3-dienes with aryl iodines and sodium dialkyl malonates has been successfully established by using a H8-BINOL-based
Nickel-Catalyzed Asymmetric Reductive Diarylation of Vinylarenes.
The application of an N-oxyl radical as a ligand to a nickel catalyst represents a novel approach to facilitate nickel-catalyzed cross-coupling reactions.
1,2-Diarylation of alkenes with aryldiazonium salts and arenes enabled by visible light photoredox catalysis.
The key to controlling the chemoselectivity toward alkene 1,2-diarylation is the employment of a 2,2'-bipyridine base, thus allowing the formation of two new C(sp3)-C(sp2) bonds via aryl radical formation from aryldiazonium salts.
Pd-Catalyzed Regioselective 1,2-Dicarbofunctionalization of Unactivated Olefins by a Heck Reaction/Enolate Cyclization Cascade.
A Pd-catalyzed reaction protocol that regioselectively difunctionalizes unactivated olefins with aryl iodides and tethered enolates is disclosed, which allows the rapid synthesis of a variety of 1,3,4-trisubstituted pyrrolidinones from simple and readily available amides.
Improved synthesis of aryl-substituted anthracenes and heteroacenes.
A Brønsted acid-catalyzed highly efficient construction of substituted arylanthracenes and heteroacenes is described, which is assumed to be initiated through the facile formation of a benzylic
A palladium-catalyzed three-component cross-coupling of conjugated dienes or terminal alkenes with vinyl triflates and boronic acids.
A three-component coupling of vinyl triflates and boronic acids to alkenes catalyzed by palladium is reported, with the reaction outcome attributed to the formation of stabilized, cationic Pd-π-allyl intermediates to regulate β-hydride elimination.
Synthesis of highly substituted naphthalene and anthracene derivatives by rhodium-catalyzed oxidative coupling of arylboronic acids with alkynes.
The rhodium-catalyzed oxidative 1:2 coupling reactions of arylboronic acids with alkynes effectively proceeds in the presence of a copper-air oxidant to produce the corresponding annulated products.