Regioselective magnesiations of functionalized arenes and heteroarenes using TMP<sub>2</sub>Mg in hydrocarbons

Hess, Andreas; Alandini, Nurtalya; Guelen, Hasret Can; Prohaska, Jan Philip; Knöchel, Paul

doi:10.1039/d2cc03856k

Cited by 4 publications

(1 citation statement)

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“…The hydrocarbon-soluble magnesium amide TMP 2 Mg (TMP = 2,2,6,6-tetramethylpiperidyl) shows excellent properties for the regioselective magnesiation of five-membered heterocycles such as imidazoles, benzoxazoles, benzofurane, and benzothiophene derivatives [27]. Imidazole and indole can be regarded as 1,3-dideaza and 1,3,7-trideaza purine.…”

Section: Organometalationsmentioning

confidence: 99%

Bond Formation at C8 in the Nucleoside and Nucleotide Purine Scaffold: An Informative Selection

Undheim

2024

Molecules

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This paper presents methods for the introduction and exchange of substituents in a nucleobase and its nucleosides and nucleotides with emphasis on the C8-position in the purine skeleton. The nucleobase is open for electrophilic and nucleophilic chemistry. The nucleophilic chemistry consists mainly of displacement reactions when the C8-substituent is a good leaving group such as a halogen atom. The heteroatom in amines, sulfides, or oxides is a good nucleophile. Halides are good reaction partners. Metal-promoted cross-coupling reactions are important for carbylations. Direct oxidative metalation reactions using sterically hindered metal amides offer chemo- and regio-selectivity besides functional tolerance and simplicity. The carbon site is highly nucleophilic after metalation and adds electrophiles resulting in chemical bond formation. Conditions for metal-assisted reactions are described for nucleobases and their glycosides.

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Section: Organometalationsmentioning

confidence: 99%

Bond Formation at C8 in the Nucleoside and Nucleotide Purine Scaffold: An Informative Selection

Undheim

2024

Molecules

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Synthesis of Tanshinone IIA and Related Terpenes via a C–H Functionalization Strategy

Tucker,

Britt,

Grover

2024

Org. Lett.

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The total synthesis of tanshinone IIA and related bioactive diterpenes isolated from the Chinese plant Salvia miltiorrhiza was completed from a common tetralin building block. The synthetic route highlights a 3,4-disubstituted furan synthesis and various regioselective C−H functionalization reactions, including a Pd catalyzed iodination and an Ir catalyzed borylation, along with an intramolecular stanna-Brook type reaction to construct the orthoquninone ring of the target molecule.

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Main group metal-mediated strategies for C–H and C–F bond activation and functionalisation of fluoroarenes

R. Judge,

Logallo,

Hevia

2023

Chem. Sci.

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Regioselective magnesiations of functionalized arenes and heteroarenes using TMP₂Mg in hydrocarbons

Abstract: We report the preparation of a new hydrocarbon-soluble magnesium amide TMP2Mg (TMP = 2,2,6,6-tetramethylpiperidyl). This base showed excellent properties for the regioselective magnesiation of various arenes and heteroarenes bearing ethyl...

Cited by 4 publications

References 39 publications

Bond Formation at C8 in the Nucleoside and Nucleotide Purine Scaffold: An Informative Selection

Bond Formation at C8 in the Nucleoside and Nucleotide Purine Scaffold: An Informative Selection

Synthesis of Tanshinone IIA and Related Terpenes via a C–H Functionalization Strategy

Main group metal-mediated strategies for C–H and C–F bond activation and functionalisation of fluoroarenes

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Regioselective magnesiations of functionalized arenes and heteroarenes using TMP2Mg in hydrocarbons

Abstract: We report the preparation of a new hydrocarbon-soluble magnesium amide TMP2Mg (TMP = 2,2,6,6-tetramethylpiperidyl). This base showed excellent properties for the regioselective magnesiation of various arenes and heteroarenes bearing ethyl...

Cited by 4 publications

References 39 publications

Bond Formation at C8 in the Nucleoside and Nucleotide Purine Scaffold: An Informative Selection

Bond Formation at C8 in the Nucleoside and Nucleotide Purine Scaffold: An Informative Selection

Synthesis of Tanshinone IIA and Related Terpenes via a C–H Functionalization Strategy

Main group metal-mediated strategies for C–H and C–F bond activation and functionalisation of fluoroarenes

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Regioselective magnesiations of functionalized arenes and heteroarenes using TMP₂Mg in hydrocarbons