1259658-97-3Relevant academic research and scientific papers
Exploration of C-H and N-H-bond functionalization towards 1-(1,2-diarylindol-3-yl)tetrahydroisoquinolines
Ghobrial, Michael,Mihovilovic, Marko D.,Schnürch, Michael
, p. 2186 - 2199 (2014)
The synthesis of 1,2,3-trisubstituted indoles was investigated. More specifically, straightforward synthetic routes towards 1-(1,2-diarylindol-3-yl)-N-PG-THIQs (PG = protecting group, THIQ = tetrahydroisoquinoline) employing transition metal-catalyzed C-H and N-H-bond functionalization were explored. It was found that the synthesis of the target compounds is strongly dependent on the order of events. Hence, depending on the requirements of a synthetic problem the most suitable and promising pathway can be chosen. Additionally, a new synthetic approach towards 1,2-diarylindoles starting from 1-arylindole could be established in the course of our investigation by using a palladium-catalyzed protocol. Such 1,2-diarylindoles were successfully reacted with N-Boc-THIQ to furnish 1,2,3-trisubstituted indoles as target compounds. Furthermore, regioselective N-arylation of protected and unprotected 1-(indol-3-yl)-THIQs was successfully conducted using either simple iron or copper salts as catalysts.
Palladium-catalyzed annulation of diarylamines with olefins through C-H activation: Direct access to N-arylindoles
Sharma, Upendra,Kancherla, Rajesh,Naveen, Togati,Agasti, Soumitra,Maiti, Debabrata
, p. 11895 - 11899 (2014)
A palladium-catalyzed dehydrogenative coupling between diarylamines and olefins has been discovered for the synthesis of substituted indoles. This intermolecular annulation approach incorporates readily available olefins for the first time and obviates the need of any additional directing group. An ortho palladation, olefin coordination, and β-migratory insertion sequence has been proposed for the generation of olefinated intermediate, which is found to produce the expected indole moiety.
On-water, microwave-assisted, Pd-catalyzed synthesis of indoles from imines and o-difunctionalized arenes
Barluenga, José,Jiménez-Aquino, Agustín,Aznar, Fernando,Valdés, Carlos
supporting information; experimental part, p. 11707 - 11711 (2010/11/04)
Regioselectively substituted indoles are prepared by a Pd-catalyzed C-C/C-N bond-forming sequence from imines and o-dihaloarenes or o-haloarene sulfonates. The heterogeneous reaction as a suspension in water and under microwave heating offers important advantages in comparison with the conventional reaction in an organic solvent, among them, operational simplicity, the employment of KOH solutions instead of alkoxides, and a dramatic reduction of reaction times.
