Barluenga, Jose; Jimenez-Aquino, Agustin; Aznar, Fernando; Valdes, Carlos published the artcile< Modular Synthesis of Indoles from Imines and o-Dihaloarenes or o-Chlorosulfonates by a Pd-Catalyzed Cascade Process>, Application In Synthesis of 35852-58-5, the main research area is palladium catalyst regioselective synthesis indole; imine preparation reaction dihaloarene halobenzenesulfonate.
A detailed study of the scope of a new Pd-catalyzed synthesis of indoles from 1,2-dihaloarenes and o-halobenzene sulfonates and imines is described. The cascade reaction comprises an imine α-arylation followed by an intramol. C-N bond-forming reaction promoted by the same Pd catalyst. The reaction with 1,2-dibromobenzene shows wide scope and allows the introduction of aryl, alkyl, and vinyl substituents at different positions of the five-membered ring of the indole. The regioselective synthesis of indoles substituted in the six-membered ring can be carried out by employing o-dihalobenzene derivatives with two different halogens, taking advantage of the different reactivities of I, Br, and Cl in oxidative addition reactions. This paper also introduces a method for the efficient cleavage of the N-t-Bu group, thus allowing for the preparation of N-H indoles through the same methodol. Finally, the reaction with o-halosulfonates has been studied. The best substrates are o-chlorononaflates, which lead to indoles in very high yield. The reaction is particularly appropriate for the synthesis of the challenging 6-substituted indoles. In view of the availability of o-chlorophenols, which are direct precursors of the chlorononaflates, this reaction represents an efficient entry into indoles substituted in the six-membered ring. The concept is illustrated by the preparation of a 4,6-disubstituted indole from naturally occurring anethole.
Journal of the American Chemical Society published new progress about Aryl halides Role: RCT (Reactant), RACT (Reactant or Reagent). 35852-58-5 belongs to class chlorides-buliding-blocks, and the molecular formula is C7H4ClF3O, Application In Synthesis of 35852-58-5.
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Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics