ABSTRACT
A palladium-catalyzed, temporary P(O) directing group assisted C-H bond arylation of carbazoles was achieved. The release of the directing group occurs spontaneously in the reaction and the mechanistic studies indicate that acid is essential for N-P bond cleavage.
ABSTRACT
With triphenylphosphine oxide serving as both the directing group and the reagent, we have developed a Cp*Ir(III)-catalyzed direct C-H functionalization of triphenylphosphine oxide with 3-diazooxindoles to afford a range of 3-(2-(diphenylphosphoryl)phenyl)indolin-2-one derivatives in moderate to excellent yields. The title products are potentially important building blocks for organic synthesis through various chemical transformations. This protocol is simple and efficient and offers high atom economy with only N2 as the byproduct.
ABSTRACT
Naphthols and 3-trifluoroethylidene oxindoles were found to undergo an asymmetric Friedel-Crafts alkylation/lactonization reaction, catalyzed by only 2.5â mol % of a quinine-derived squaramide catalyst, to afford the corresponding α-aryl-ß-trifluoromethyl dihydrocoumarin derivatives in high yields (up to 99 %) with excellent enantio- and diastereoselectivities (up to 98 % ee, >20:1 d.r.). Importantly, the lactonization proceeded by nucleophilic attack of the naphthol hydroxy group at the amide motif of the oxindoles under mild reaction conditions. This protocol represents a new strategy for the formation of dihydrocoumarins by an efficient intramolecular amide C-N bond-cleavage and esterification process.
ABSTRACT
A highly enantioselective C2 Friedel-Crafts alkylation reaction of 3-substituted indoles to ß,γ-unsaturated α-ketimino esters has been developed. This reaction was efficiently catalyzed by a chiral phosphoric acid catalyst. The corresponding C2-substituted indole derivatives, bearing an α-ketimino ester motif, were obtained in moderate to high yields (up to 93%) and with high enantioselectivities (up to >99% ee).
