Alkynylation‐Desilylation‐Alkynylation‐Cycloisomerization (ADAC) Three‐Component Synthesis of 2,2′‐Biindolyls – Concise Synthesis of Tjipanazole I

Kustosz, Sebastian; Niesobski, Patrik; Müller, Thomas J. J.

doi:10.1002/cctc.202001607

Cited by 3 publications

(3 citation statements)

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“…A Communication by Müller and colleagues describes an elegant one‐pot Pd/Cu‐catalyzed alkynylation/desilylation/alkynylation/cycloisomerization (ADAC) process, which provides rapid and efficient access to 2,2′‐biindolyls, employed in a concise two‐step synthesis of the alga alkaloid tjipanazole I [8] . An elegant cascade process towards challenging oligocyclic systems through the combination of a formal anti ‐carbopalladation with a Suzuki cross‐coupling, was devised by the Werz group [9] .…”

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confidence: 99%

“…[7] A Communication by Müller and colleagues describes an elegant one-pot Pd/Cu-catalyzed alkynylation/desilylation/alkynylation/cycloisomerization (ADAC) process, which provides rapid and efficient access to 2,2'-biindolyls, employed in a concise two-step synthesis of the alga alkaloid tjipanazole I. [8] An elegant cascade process towards challenging oligocyclic systems through the combination of a formal anti-carbopalladation with a Suzuki cross-coupling, was devised by the Werz group. [9] A further cascade process by means of an efficient domino relay metathesis sequences using triallyl 3-oxindole and indole precursors to access fused bicyclic indoxyl dimers and carbazole derivatives is described in the Communication by the Dash group, [10] while a ligand-and additive-free process developed by the Hoover group allows a straightforward aerobic cobalt-catalyzed synthesis of 2-aminobenzimidazoles starting from 2-aminoanilines.…”

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Editorial: The Catalysis of Ring Synthesis

2021

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Ring systems -aromatic or non-aromatic carbocyclic and heterocyclic structures -represent key scaffolds in biologically important molecules. In particular, heterocycles are fundamental building blocks of most small-molecule drugs on the market today. Furthermore, aromatic and heteroaromatic ring systems are of eminent importance for material sciences and are playing a significant role as chromophores, liquid crystalline materials, molecular receptors, redox materials, organic light-emitting diodes, and photochemical switches, etc.Catalysis, including transition-metal catalysis, organocatalysis, nanocatalysis, photoredox catalysis, has become as a powerful tool for the synthesis of different ring systems. This Special Collection "The Catalysis of Ring Synthesis" covers the most recent strategies of ring synthesis and presents the current advances in the field.A Review by Kotha and co-authors summarizes new synthetic methods to diverse cage polycycles potentially useful for high energy density materials synthesis. [1] In the Review paper by Neto and Zeni the diverse variety of synthesis of pyrrole derivatives using the reaction of alkynes with nitrogencompounds under transition metal-catalyzed and metal-free conditions, is presented. [2] A Minireview from the group of Das reflects the impressive state of the art in photoredox catalysis and the recent applications of photocatalysis to [2 + 2] and [4 + 2] cycloaddition reactions under the irradiation of visible light. [3] Efficient organocatalyzed and/or transition-metal-catalyzed synthesis of azirine, pyridine, piperidine, indole, indoxyl, benzimidazole, carbazole, spiro pyrrolidone, γ-(thio)butyrolactone, quinolone derivatives and oligocyclic systems are reported in a total of 12 Communications. A highly efficient enantioselective organocatalytic synthesis of trisubstituted [a]

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Editorial: The Catalysis of Ring Synthesis

2021

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“…Among others, this 3-component reaction was used to construct tjipanazole I. 20 The 1,1′-bisindole Schischkiniin (Fig. 1) was isolated from the seeds of the thistle Centaurea schischkinii by Sarker et al 21 Various plants of the genus Centaurea have long been used in traditional medicine to treat, for example, diabetes, diarrhea, rheumatism, malaria, and hypertension.…”

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Efficient approach to 1,1′-bisindoles via copper(i)-catalyzed double domino reaction

Bauer,

Conrad,

Beifuss

2023

Org. Biomol. Chem.

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Recent Advances in Sequentially Pd-Catalyzed One-Pot Syntheses of Heterocycles

Kornet,

Müller

2024

Molecules

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Sequential Pd-catalyzed one-pot synthetic methodologies have emerged as a powerful and versatile approach in organic synthesis, enabling the construction of complex heterocyclic architectures with high efficiency, selectivity, and atom economy. This review discusses key advancements in multistep, sequentially Pd-catalyzed one-pot processes for accessing heterocyclic derivatives, focusing on classic reactions like Suzuki–Miyaura, Sonogashira, Heck, and hydroamination and extending to specialized techniques such as directed C-H activation. The concatenation of these steps has advanced the scope of one-pot strategies. A section is dedicated to exploring the cooperative use of palladium with other metals, particularly copper, ruthenium, and gold, which has broadened the range of accessible heterocyclic derivatives. Highlighted applications include the synthesis of biologically and pharmaceutically relevant compounds, such as tris(hetero)aryl systems, spiro-oxindoles, and indole derivatives. These one-pot strategies not only streamline synthesis but also align with green chemistry principles by minimizing purification steps and reducing waste and energy consumption. The review also addresses current challenges and limitations in these methodologies, offering insights into ongoing efforts to optimize reaction conditions and expand the applicability of sequential Pd-catalyzed processes.

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Alkynylation‐Desilylation‐Alkynylation‐Cycloisomerization (ADAC) Three‐Component Synthesis of 2,2′‐Biindolyls – Concise Synthesis of Tjipanazole I

Cited by 3 publications

References 55 publications

Editorial: The Catalysis of Ring Synthesis

Editorial: The Catalysis of Ring Synthesis

Efficient approach to 1,1′-bisindoles via copper(i)-catalyzed double domino reaction

Recent Advances in Sequentially Pd-Catalyzed One-Pot Syntheses of Heterocycles

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