Synthesis of 3-arylated indolines from dearomatization of indoles

Electrochemical Dearomative Dihydroxylation and Hydroxycyclization of Indoles

“…[2] The related electrochemical dearomative 1,2-difunctionalization of (hetero)arenes and in particular indoles has been less studied. [3][4][5][6][7][8] The dearomatization of indole, for which we have been interested for almost a decade, [9,10] generates three dimensional indolines of potential biological relevance. [11] In few cases, dearomative electrolysis could be performed from an NÀ H indole substrate [6] as it was demonstrated by Harran during the 60 gram-scale synthesis of the benzofuroindoline core of DZ-2384, a highly potent antitumoral agent inspired by the natural product diazonamide A.…”

Silver-Mediated Intramolecular Friedel–Crafts-Type Cyclizations of 2-Benzyloxy-3-bromoindolines: Synthesis of Isochromeno[3,4-b] indolines and 3-Arylindoles

“…6 On the other hand, the synthesis of isochromeno [3,4-b]indolines has scarcely developed until recently because of their complex structures including 3-arylindolines. 7 In 2017, Vincent and co-workers reported a silver-mediated oxidative coupling of indoles and tetrahydro--carbolines with 2,3-dihydroxybenzoic acids for the construction of isochromeno [3,4-b]indolines, affording the total synthesis of voacalgine A and bipleiophylline (Scheme 1A). 8 As a catalytic version of the oxidative coupling, Chen and co-workers developed the Fe-mediated oxidative cou-pling of indoles with 2,3-dihydroxybenzoic acids (Scheme 1B).…”

Oxidative Coupling of 3‐Oxindoles with Indoles and Arenes

“…The reported method, although diastereoselective, has limited scope and moderate yields. Other 3‐aryl indolines are readily accessible through a variety of oxidation methods …”