Synthesis of substituted γ- and δ-lactams based on titanocene(<scp>iii</scp>)-catalysed radical cyclisations of trichloroacetamides

Diaba, Fai͏̈za; Gómez‐Bengoa, Enrique; Cuerva, Juan M.; Bonjoch, Josep; Justicia, José

doi:10.1039/c6ra12180b

Cited by 5 publications

(1 citation statement)

References 64 publications

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“…Recently, biscyclopentadienyltitanium(III) chloride (Cp 2 TiCl), 69 was introduced to generate dichloromethylcarbamoyl radicals, e.g., for 96a, under mild conditions to afford fully reduced lactam 28f (Scheme 56). 70 Mn dust and TMSCl/2,4,6-collidine were used to regenerate the titanocene(III) species. The proton source was assumed to be the THF.…”

Section: Titanocene(iii)-catalyzed Reactionsmentioning

confidence: 99%

Radical Cyclization of Trichloroacetamides: Synthesis of Lactams

Coussanes¹,

Vilà²,

Diaba³

et al. 2017

Synthesis

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Trichloroacetamides can act as radical precursors to synthesize nitrogen-containing heterocycles in a variety of processes, mainly involving atom transfer radical cyclizations (ATRC), mediated by Cu(I) or Ru(II) catalysts, and the hydride reductive method, employing either Bu 3 SnH or (Me 3 Si) 3 SiH, or recently NaBH 3 CN. Additionally, amine-mediated single-electron transfer cyclizations, as well as radical processes promoted by Ni, Fe, Mn, Ti, and Ag, have been developed. 1 Introduction 2 Atom Transfer Radical Cyclizations (ATRC) 2.

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Section: Titanocene(iii)-catalyzed Reactionsmentioning

confidence: 99%

Radical Cyclization of Trichloroacetamides: Synthesis of Lactams

Coussanes¹,

Vilà²,

Diaba³

et al. 2017

Synthesis

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Development, Scope, and Applications of Titanium(III)‐Catalyzed Cyclizations to Aminated N‐Heterocycles

Leijendekker

Weweler

Leuther

et al. 2019

Chemistry A European J

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The exceptionally mild conditions of at itanium(III)-catalyzed cyclization reactionp aired with ac onvenient acid/base extraction have enabled the straightforward synthesis, isolation, and direct N-functionalization of amino heterocycles such as 3-aminoindoles and -pyrroles.T he unprotected heterocycles are ideal building blocks fort he installation of aminatedi ndoles and pyrroles into target molecules, but their sensitivity has previously impeded their synthesis by modernc atalytic methods. This full paper presents the development and extended scope of the new cyclization methodology.T he transformation of the products into fused bis-indoles is also demonstrated along with the discoveryo f an unusual palladium-catalyzed reductive biphenyl coupling reaction. The titanium(III)-catalyzed cyclization hasa lso been appliedt ot he synthesis of substituted 3-iminoindolines, which are of potential interestf or applicationsi nn atural product synthesis and exhibit tunable blue-to-green fluorescence properties.Supporting information and the ORCID identification number(s) for the author(s) of this articlecan be found under: https://doi.org/10.1002/chem.201805909.Scheme1.a) Usualand ideal scenarios for the catalytic synthesis of 3-aminoindole and -pyrrole building blocks. b) Envisionedtitanium(III)-catalyzed cyclization to furnish unprotected, electron-rich 3-aminoheterocycles.

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ChemInform Abstract: Synthesis of Substituted γ‐ and δ‐Lactams Based on Titanocene(III)‐Catalyzed Radical Cyclizations of Trichloroacetamides.

Diaba¹,

Gómez‐Bengoa²,

Cuerva³

et al. 2016

ChemInform

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Synthesis of substituted γ- and δ-lactams based on titanocene(iii)-catalysed radical cyclisations of trichloroacetamides

Abstract: Straightforward synthesis of dehalogenated γ- and δ-lactams based on a Cp2TiCl-catalysed radical cyclisation of trichloroacetamides under mild conditions.

Cited by 5 publications

References 64 publications

Radical Cyclization of Trichloroacetamides: Synthesis of Lactams

Radical Cyclization of Trichloroacetamides: Synthesis of Lactams

Development, Scope, and Applications of Titanium(III)‐Catalyzed Cyclizations to Aminated N‐Heterocycles

ChemInform Abstract: Synthesis of Substituted γ‐ and δ‐Lactams Based on Titanocene(III)‐Catalyzed Radical Cyclizations of Trichloroacetamides.

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