Organic acid catalysed Minisci-type arylation of heterocycles with aryl acyl peroxides

Ouyang, Yani; Yue, Xiao‐Guang; Peng, Jiehai; Zhu, Jiashun; Shen, Qiuyuan; Li, Wanmei

doi:10.1039/d2ob01187e

Cited by 4 publications

(1 citation statement)

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“…For example, Li and coworkers 409 have recently reported that the mild thermal treatment of dibenzoyl peroxide (Ph− COO) 2 generates Ph−COO • radicals that lead to Ph • radicals after decarboxylation. The latter can then attack phen in position 2, leading to 202 (Scheme 68).…”

Section: Activation Of C 2 By Coordination Of Metal Ionsmentioning

confidence: 99%

Fifty Shades of Phenanthroline: Synthesis Strategies to Functionalize 1,10-Phenanthroline in All Positions

Queffélec,

Pati,

Pellegrin

2024

Chem. Rev.

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1,10-Phenanthroline (phen) is one of the most popular ligands ever used in coordination chemistry due to its strong affinity for a wide range of metals with various oxidation states. Its polyaromatic structure provides robustness and rigidity, leading to intriguing features in numerous fields (luminescent coordination scaffolds, catalysis, supramolecular chemistry, sensors, theranostics, etc.). Importantly, phen offers eight distinct positions for functional groups to be attached, showcasing remarkable versatility for such a simple ligand. As a result, phen has become a landmark molecule for coordination chemists, serving as a must-use ligand and a versatile platform for designing polyfunctional arrays. The extensive use of substituted phenanthroline ligands with different metal ions has resulted in a diverse array of complexes tailored for numerous applications. For instance, these complexes have been utilized as sensitizers in dye-sensitized solar cells, as luminescent probes modified with antibodies for biomaterials, and in the creation of elegant supramolecular architectures like rotaxanes and catenanes, exemplified by Sauvage’s Nobel Prize-winning work in 2016. In summary, phen has found applications in almost every facet of chemistry. An intriguing aspect of phen is the specific reactivity of each pair of carbon atoms ([2,9], [3,8], [4,7], and [5,6]), enabling the functionalization of each pair with different groups and leading to polyfunctional arrays. Furthermore, it is possible to differentiate each position in these pairs, resulting in non-symmetrical systems with tremendous versatility. In this Review, the authors aim to compile and categorize existing synthetic strategies for the stepwise polyfunctionalization of phen in various positions. This comprehensive toolbox will aid coordination chemists in designing virtually any polyfunctional ligand. The survey will encompass seminal work from the 1950s to the present day. The scope of the Review will be limited to 1,10-phenanthroline, excluding ligands with more intracyclic heteroatoms or fused aromatic cycles. Overall, the primary goal of this Review is to highlight both old and recent synthetic strategies that find applicability in the mentioned applications. By doing so, the authors hope to establish a first reference for phenanthroline synthesis, covering all possible positions on the backbone, and hope to inspire all concerned chemists to devise new strategies that have not yet been explored.

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Section: Activation Of C 2 By Coordination Of Metal Ionsmentioning

confidence: 99%

Fifty Shades of Phenanthroline: Synthesis Strategies to Functionalize 1,10-Phenanthroline in All Positions

Queffélec,

Pati,

Pellegrin

2024

Chem. Rev.

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Regioselective Synthesis of Phenanthridines via Pd(II)-Catalyzed Annulative C(sp²)–H Activation

Yadav,

Upadhyay,

Kant

et al. 2023

J. Org. Chem.

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A robust synthesis of phenanthridines has been described via Pd(II)-catalyzed domino C(sp2)–H activation/N-arylation using oxime esters with aryl acyl peroxides in a highly regioselective manner. This protocol is compatible with acetophenone as well as benzophenone-derived oxime esters and allows modular construction of functionalized phenanthridines with wide tolerance of electronic functionality. Further transformations were conducted to synthesize key building blocks, and control experiments were performed to understand the plausible reaction mechanism.

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Minisci-Type Dehydrogenative Coupling of N-Heteroaromatic Rings with Inert C(sp³)–H Enabled by a Visible-Light-Catalyzed Intermolecular Hydrogen Atom Transfer Process

Yang,

Liu,

Wei

et al. 2024

J. Org. Chem.

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The Minisci-type dehydrogenative coupling of N-heteroaromatic rings with inert C–H or Si–H partners via visible-light-catalyzed hydrogen atom transfer has been reported. This methodology allows the coupling reactions to be carried out in water as a solvent under air atmospheric conditions with visible-light illumination. A wide range of inert C–H and Si–H partners could be directly coupled with various N-aromatic heterocycles to deliver products in good to excellent yields.

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Organic acid catalysed Minisci-type arylation of heterocycles with aryl acyl peroxides

Abstract: A metal-free method for the Minisci-type arylation of heterocycles with aryl acyl peroxides has been reported. This strategy enables the rapid and simple synthesis of a series of Minisci-type adducts...

Cited by 4 publications

References 83 publications

Fifty Shades of Phenanthroline: Synthesis Strategies to Functionalize 1,10-Phenanthroline in All Positions

Fifty Shades of Phenanthroline: Synthesis Strategies to Functionalize 1,10-Phenanthroline in All Positions

Regioselective Synthesis of Phenanthridines via Pd(II)-Catalyzed Annulative C(sp²)–H Activation

Minisci-Type Dehydrogenative Coupling of N-Heteroaromatic Rings with Inert C(sp³)–H Enabled by a Visible-Light-Catalyzed Intermolecular Hydrogen Atom Transfer Process

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Organic acid catalysed Minisci-type arylation of heterocycles with aryl acyl peroxides

Abstract: A metal-free method for the Minisci-type arylation of heterocycles with aryl acyl peroxides has been reported. This strategy enables the rapid and simple synthesis of a series of Minisci-type adducts...

Cited by 4 publications

References 83 publications

Fifty Shades of Phenanthroline: Synthesis Strategies to Functionalize 1,10-Phenanthroline in All Positions

Fifty Shades of Phenanthroline: Synthesis Strategies to Functionalize 1,10-Phenanthroline in All Positions

Regioselective Synthesis of Phenanthridines via Pd(II)-Catalyzed Annulative C(sp2)–H Activation

Minisci-Type Dehydrogenative Coupling of N-Heteroaromatic Rings with Inert C(sp3)–H Enabled by a Visible-Light-Catalyzed Intermolecular Hydrogen Atom Transfer Process

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Regioselective Synthesis of Phenanthridines via Pd(II)-Catalyzed Annulative C(sp²)–H Activation

Minisci-Type Dehydrogenative Coupling of N-Heteroaromatic Rings with Inert C(sp³)–H Enabled by a Visible-Light-Catalyzed Intermolecular Hydrogen Atom Transfer Process