Katalytische reduktive Synthese und direkte Derivatisierung ungeschützter Aminoindole, Aminopyrrole und Iminoindoline

Leijendekker, Leonardus H.; Weweler, Jens; Leuther, Tobias M.; Streuff, Jan

doi:10.1002/ange.201702310

Angewandte Chemie

2017

DOI: 10.1002/ange.201702310

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Katalytische reduktive Synthese und direkte Derivatisierung ungeschützter Aminoindole, Aminopyrrole und Iminoindoline

Leonardus H. Leijendekker

Jens Weweler

Tobias M. Leuther

et al.

Abstract: Es wird eine Titan(III)-katalysierte Radikalcyclisierung zu ungeschützten 3-Aminoindolen, 3-Aminopyrrolen oder 3-Iminoindolinen vorgestellt. Die Reaktion ist ungefährlich,skalierbar und ermçglicht die leichte Isolierung der freien Produkte mittels Extraktion. Die Methode zeigt eine große Substratbandbreite auf und ermçglicht die direkte Stickstoffschützung oder Synthese von Peptidbausteinen in einer einzelnen Sequenz. Anellierte Bisindole sind ebenfalls aus den Cyclisierungsprodukten zugänglich.

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Cited by 10 publications

References 59 publications

(39 reference statements)

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Trimethylsilyl‐Protected Alkynes as Selective Cross‐Coupling Partners in Titanium‐Catalyzed [2+2+1] Pyrrole Synthesis

Chiu

Tonks

2018

Angewandte Chemie

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Trimethylsilyl (TMS)-protected alkynes served as selective alkyne cross-coupling partners in titanium-catalyzed [2+ +2+ +1] pyrrole synthesis.R eactions of TMS-protected alkynes with internal alkynes and azobenzene under the catalysis of titanium imido complexes yielded pentasubstituted 2-TMS-pyrroles with greater than 90 %s electivity over the other nine possible pyrrole products.The steric and electronic effects of the TMS group were both identified to playkey roles in this highly selective pyrrole synthesis.This strategy provides aconvenient method to synthesize multisubstituted pyrroles as well as an entry point for further pyrrole diversification through facile modification of the resulting 2-silyl pyrrole products,asdemonstrated through ashort formal synthesis of the marine natural product lamellarin R.

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Trimethylsilyl‐Protected Alkynes as Selective Cross‐Coupling Partners in Titanium‐Catalyzed [2+2+1] Pyrrole Synthesis

Chiu

Tonks

2018

Angewandte Chemie

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Mechanism‐Based Condition Screening for Sustainable Catalysis in Single‐Electron Steps by Cyclic Voltammetry

et al. 2018

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Ac yclic-voltammetry-based screening method for Cp 2 TiX-catalyzed reactions is introduced. Our mechanismbased approach enables the study of the influence of various additives on the electrochemically generated active catalyst Cp 2 TiX, which is in equilibrium with catalytically inactive [Cp 2 TiX 2 ] À .T hioureas and ureas are most efficient in the generation of Cp 2 TiXinTHF.Knowing the precise position of the equilibrium between Cp 2 TiXand [Cp 2 TiX 2 ] À allowed us to identify reaction conditions for the bulk electrolysis of Cp 2 TiX 2 complexes and for Cp 2 TiX-catayzed radical arylations without having to carry out the reactions.O ur time-and resourceefficient approach is of general interest for the design of catalytic reactions that proceed in single-electron steps.Catalysis in single-electron steps [1] and metalloradical catal-

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Titan(III)‐katalysierte, reduktive Decyanierung geminaler Dinitrile ohne freie Radikalintermediate

2019

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Es wird über eine titankatalysierte Monodecyanierung geminaler Dinitrile berichtet, die unter milden Bedingungen abläuft, zahlreiche funktionelle Gruppen toleriert und aucha uf quartäre Malononitrile angewendet werden kann. Eine entsprechende Desulfonylierung wird ebenfalls vorgestellt. MechanistischeU ntersuchungen unterstützen eine katalysatorkontrollierte Spaltung ohne freie Radikale,w as im Gegensatz zu den bisherigen stçchiometrischen radikalischen Decyanierungen steht. Die Beteiligung zweier Ti III -Spezies an der C-C-Bindunsspaltung wird vorgeschlagen und die Rolle der Additive ZnCl 2 und Coll·HCl näher untersucht. Schema 1. Stçchiometrische, radikalische Decyanierungen und die hier vorgestellte Titan(III)-Katalyse.

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Katalytische reduktive Synthese und direkte Derivatisierung ungeschützter Aminoindole, Aminopyrrole und Iminoindoline

Cited by 10 publications

References 59 publications

Trimethylsilyl‐Protected Alkynes as Selective Cross‐Coupling Partners in Titanium‐Catalyzed [2+2+1] Pyrrole Synthesis

Trimethylsilyl‐Protected Alkynes as Selective Cross‐Coupling Partners in Titanium‐Catalyzed [2+2+1] Pyrrole Synthesis

Mechanism‐Based Condition Screening for Sustainable Catalysis in Single‐Electron Steps by Cyclic Voltammetry

Titan(III)‐katalysierte, reduktive Decyanierung geminaler Dinitrile ohne freie Radikalintermediate

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