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Two‐in‐One Strategy for Palladium‐Catalyzed C−H Functionalization in Water

“…The tetrahydro‐β‐carboline skeleton bearing a quaternary carbon center at C1 is an important framework in natural products and pharmaceutical agents (Figure ). Examples include Komavine ( 1 ) (and Acetylkomavine), Spiroindolone ( 2 ), Tabertinggine ( 3 ), Peharmaline A ( 4 ), Subincanadine B ( 5 ), and the antimalarial drug NITD609 ( 6 ) . Herein, based on the two‐in‐one strategy, we report a palladium‐catalyzed C−H bond activation at C2 of indole and pyridine in water followed by cyclization with a transient directing group (imine group) to form the C−C bond.…”

Analytical characterisation of the routes by thermolytic decarboxylation from tryptophan to tryptamine using ketone catalysts, resulting in tetrahydro-β-carboline formation

“…The spirocyclohexane-THBC 8 komavine has been isolated from plants of the Nitraria genus and its pharmacology is unknown [51]. Some of these plants have been reported to show vasoactive, serotonin-like activity, which however was attributed to other alkaloids than 8 [52].…”

Two‐in‐One Strategy for Palladium‐Catalyzed C−H Functionalization in Water

“…Deuterium-labeling experiments are discussed to provide insight into the mechanism. Examples include Komavine (1)( and Acetylkomavine), [4] Spiroindolone (2), [5] Tabertinggine (3), [6] Peharmaline A( 4), [7] Subincanadine B(5), [8] and the antimalarial drug NITD609 (6). As only aminute difference in reactivity exists between various CÀHb onds,r egioselective activation of these CÀHb onds constitutes ag reat challenge.T os olve such ap roblem, ad irecting group can help to direct the catalyst to activate proximal C À Hb onds via cyclometallated intermediates.However,the directing group needs to be preinstalled in the substrate and, upon finishing its mission, it is usually hard to remove from the product (Scheme 1a).…”

“…[3] Forg reener and more atom-economical transformations,a s well as taking into consideration the difficulty in separating the reversibly linked directing group from the product, the development of a" two-in-one" strategy for C À Hf unctionalization, in which the transient directing group is also used as ar eagent to react with the activated CÀHb ond, is highly attractive.Thetetrahydro-b-carboline skeleton bearing aquaternary carbon center at C1 is an important framework in natural products and pharmaceutical agents (Figure 1). Examples include Komavine (1)( and Acetylkomavine), [4] Spiroindolone (2), [5] Tabertinggine (3), [6] Peharmaline A( 4), [7] Subincanadine B(5), [8] and the antimalarial drug NITD609 (6). [9] Herein, based on the two-in-one strategy,w er eport ap alladium-catalyzed CÀHb ond activation at C2 of indole and pyridine in water followed by cyclization with at ransient directing group (imine group) to form the C À Cb ond.…”

“…Thetetrahydro-b-carboline skeleton bearing aquaternary carbon center at C1 is an important framework in natural products and pharmaceutical agents ( Figure 1). Examples include Komavine (1)( and Acetylkomavine), [4] Spiroindolone (2), [5] Tabertinggine (3), [6] Peharmaline A( 4), [7] Subincanadine B(5), [8] and the antimalarial drug NITD609 (6). [9] Herein, based on the two-in-one strategy,w er eport ap alladium-catalyzed CÀHb ond activation at C2 of indole and pyridine in water followed by cyclization with at ransient directing group (imine group) to form the C À Cb ond.…”