Synthesis and Functionalization of Indoles through Rhodium-Catalyzed Reactions

Patil, Shivaputra A.; Patil, Renukadevi

doi:10.2174/157017907780598862

Cited by 29 publications

(2 citation statements)

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“…Transition metal catalysis, especially incorporating Rh(III)-catalyzed pathways, is more substantial toward the functionalization of indoles in a rapid manner . Along with that, as mentioned earlier, the limitations are also overcome by the typical use of Rh-benzannulation protocols . The benzannulation term was originally adopted from the Latin word indicating the formation of two new bonds in the rapid “anellus method” .…”

Section: Introductionmentioning

confidence: 99%

“… 36 Along with that, as mentioned earlier, the limitations are also overcome by the typical use of Rh-benzannulation protocols. 37 The benzannulation term was originally adopted from the Latin word indicating the formation of two new bonds in the rapid “anellus method”. 38 Gratifyingly, Rh-catalyzed benzannulations are promising and scalable techniques in modern organic synthesis pursuits in which new rings are formed over a pre-existing scaffold efficiently.…”

Section: Introductionmentioning

confidence: 99%

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[RhCp*Cl₂]₂-Catalyzed Indole Functionalization: Synthesis of Bioinspired Indole-Fused Polycycles

Singh Chauhan,

Mali,

Dua

et al. 2023

ACS Omega

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Polycyclic fused indoles are ubiquitous in natural products and pharmaceuticals due to their immense structural diversity and biological inference, making them suitable for charting broader chemical space. Indole-based polycycles continue to be fascinating as well as challenging targets for synthetic fabrication because of their characteristic structural frameworks possessing biologically intriguing compounds of both natural and synthetic origin. As a result, an assortment of new chemical processes and catalytic routes has been established to provide unified access to these skeletons in a very efficient and selective manner. Transition-metal-catalyzed processes, in particular from rhodium(III), are widely used in synthetic endeavors to increase molecular complexity efficiently. In recent years, this has resulted in significant progress in reaching molecular scaffolds with enormous biological activity based on core indole skeletons. Additionally, Rh(III)-catalyzed direct C–H functionalization and benzannulation protocols of indole moieties were one of the most alluring synthetic techniques to generate indole-fused polycyclic molecules efficiently. This review sheds light on recent developments toward synthesizing fused indoles by cascade annulation methods using Rh(III)-[RhCp*Cl2]2-catalyzed pathways, which align with the comprehensive and sophisticated developments in the field of Rh(III)-catalyzed indole functionalization. Here, we looked at a few intriguing cascade-based synthetic designs catalyzed by Rh(III) that produced elaborate frameworks inspired by indole bioactivity. The review also strongly emphasizes mechanistic insights for reaching 1–2, 2–3, and 3–4-fused indole systems, focusing on Rh(III)-catalyzed routes. With an emphasis on synthetic efficiency and product diversity, synthetic methods of chosen polycyclic carbocycles and heterocycles with at least three fused, bridged, or spiro cages are reviewed. The newly created synthesis concepts or toolkits for accessing diazepine, indol-ones, carbazoles, and benzo-indoles, as well as illustrative privileged synthetic techniques, are included in the featured collection.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

[RhCp*Cl₂]₂-Catalyzed Indole Functionalization: Synthesis of Bioinspired Indole-Fused Polycycles

Singh Chauhan,

Mali,

Dua

et al. 2023

ACS Omega

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Indoles via Palladium‐Catalyzed Cyclization

2011

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The palladium‐catalyzed assembly of the functionalized pyrrole nucleus on a benzenoid scaffold is a widley used synthetic tool for the preparation of indole derivatives. This construction can be categorized into four main types: (1) cyclization of alkynes; (2) cyclization of alkenes; (3) cyclization via C ‐vinyl reactions; and (4) cyclization via N − arylation or N − vinylation reactions. The first approach is the most versatile in terms of range of the added functional groups and of the bonds that can be created in the construction of the pyrrole ring. This method is based on the utilization of precursors containing nitrogen nucleophiles and carbon‐carbon triple bonds. The nitrogen nucleophile and alkyne moiety may be part of the same molecule or belong to two different molecules. Some of the most general cyclizations of indoles are summarized. Alkene‐based cyclizations to give indoles are also summarized. Cyclization to indoles via arene vinylation has limited synthetic scope. Indoles can be prepared via cyclizations proceeding through N ‐arylation and N‐vinylation reactions based on pioneering work. In general, only synthetic procedures where palladium catalysis is involved in the pryrrole ring construction event are discussed in this chapter.

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Rhodium‐Catalyzed Indole Ring Synthesis

Gribble

2016

Indole Ring Synthesis

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Synthesis and Functionalization of Indoles through Rhodium-Catalyzed Reactions

Cited by 29 publications

References 88 publications

[RhCp*Cl₂]₂-Catalyzed Indole Functionalization: Synthesis of Bioinspired Indole-Fused Polycycles

[RhCp*Cl₂]₂-Catalyzed Indole Functionalization: Synthesis of Bioinspired Indole-Fused Polycycles

Indoles via Palladium‐Catalyzed Cyclization

Rhodium‐Catalyzed Indole Ring Synthesis

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Synthesis and Functionalization of Indoles through Rhodium-Catalyzed Reactions

Cited by 29 publications

References 88 publications

[RhCp*Cl2]2-Catalyzed Indole Functionalization: Synthesis of Bioinspired Indole-Fused Polycycles

[RhCp*Cl2]2-Catalyzed Indole Functionalization: Synthesis of Bioinspired Indole-Fused Polycycles

Indoles via Palladium‐Catalyzed Cyclization

Rhodium‐Catalyzed Indole Ring Synthesis

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[RhCp*Cl₂]₂-Catalyzed Indole Functionalization: Synthesis of Bioinspired Indole-Fused Polycycles

[RhCp*Cl₂]₂-Catalyzed Indole Functionalization: Synthesis of Bioinspired Indole-Fused Polycycles