Brønsted acid-catalyzed C-H Functionalisation of N-Protected 
Tetrahydroisoquinolines via Intermediate Peroxides

Schweitzer-Chaput, Bertrand; Klußmann, Martin

doi:10.1002/ejoc.201201527

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Brønsted acid-catalyzed C-H Functionalisation of N-Protected Tetrahydroisoquinolines via Intermediate Peroxides

Schweitzer-Chaput, B., & Klußmann, M. (2013). Brønsted acid-catalyzed C-H Functionalisation of N-Protected Tetrahydroisoquinolines via Intermediate Peroxides. European Journal of Organic Chemistry, 2013(4), 666-671. doi:10.1002/ejoc.201201527.

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Item Permalink: https://hdl.handle.net/11858/00-001M-0000-0014-A517-D Version Permalink: https://hdl.handle.net/11858/00-001M-0000-0024-A808-E

Genre: Journal Article

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Creators:
Schweitzer-Chaput, Bertrand¹, Author
Klußmann, Martin¹, Author

Affiliations:
1Research Group Klußmann, Max-Planck-Institut für Kohlenforschung, Max Planck Society, Kaiser-Wilhelm-Platz 1, 45470 Mülheim an der Ruhr, ou_1445608

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Free keywords: DEHYDROGENATIVE COUPLING REACTION; CARBON-HYDROGEN BONDS; TERTIARY-AMINES; NITROGEN ATOM; OXIDATIVE CYANATION; SODIUM-CYANIDE; ADJACENT; NUCLEOPHILICITY; AMIDOALKYLATION; ALKYNYLATION

Abstract: An organocatalytic oxidative synthesis of N-protected tetrahydroisoquinolines is described by C–H functionalization via intermediate peroxides. The peroxides were synthesized from tert-butylhydroperoxide under metal-free thermal conditions and were converted into the final products by Brønsted acid catalyzed substitution. The nucleophile scope was investigated in detail and proved to be broad; N-deprotection of the coupling products could also be achieved.

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Language(s): eng - English

Dates: Submitted: 2012-11-14Published Online: 2012-12-13Date issued: 2013-02

Publication Status: Issued

Pages: 6

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Table of Contents: -

Rev. Type: Peer

Identifiers: DOI: 10.1002/ejoc.201201527

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Title: European Journal of Organic Chemistry

Other : Eur. J. Org. Chem.

Source Genre: Journal

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Publ. Info: Weinheim, Germany : Wiley-VCH Verlag GmbH

Pages: - Volume / Issue: 2013 (4) Sequence Number: - Start / End Page: 666 - 671 Identifier: ISSN: 1434-193X
CoNE: https://pure.mpg.de/cone/journals/resource/954926953810