Thiosemicarbazone organocatalysis: Tetrahydropyranylation and 2-deoxygalactosylation reactions and kinetics-based mechanistic investigation

Dennis Larsen, Line M. Langhorn, Olivia M. Akselsen, Bjarne E. Nielsen, Michael Pittelkow*

*Corresponding author for this work

Research output: Contribution to journalJournal articleResearchpeer-review

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Abstract

The first use of thiosemicarbazone-based organocatalysis was demonstrated on both tetrahydropyranylation and 2-deoxygalactosylation reactions. The organocatalysts were optimised using kinetics-based selection. The best catalyst outperformed previously reported thiourea catalysts for tetrahydropyranylation by 50-fold. Hammett investigations of both the organocatalyst and the substrate indicate an oxyanion hole-like reaction mechanism.

Original languageEnglish
JournalChemical Science
Volume8
Issue number12
Pages (from-to)7978-7982
Number of pages5
ISSN2041-6520
DOIs
Publication statusPublished - 2017

Cite this

Larsen, Dennis ; Langhorn, Line M. ; Akselsen, Olivia M. ; Nielsen, Bjarne E. ; Pittelkow, Michael. / Thiosemicarbazone organocatalysis : Tetrahydropyranylation and 2-deoxygalactosylation reactions and kinetics-based mechanistic investigation. In: Chemical Science. 2017 ; Vol. 8, No. 12. pp. 7978-7982.
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abstract = "The first use of thiosemicarbazone-based organocatalysis was demonstrated on both tetrahydropyranylation and 2-deoxygalactosylation reactions. The organocatalysts were optimised using kinetics-based selection. The best catalyst outperformed previously reported thiourea catalysts for tetrahydropyranylation by 50-fold. Hammett investigations of both the organocatalyst and the substrate indicate an oxyanion hole-like reaction mechanism.",
author = "Dennis Larsen and Langhorn, {Line M.} and Akselsen, {Olivia M.} and Nielsen, {Bjarne E.} and Michael Pittelkow",
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doi = "10.1039/c7sc03366d",
language = "English",
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publisher = "Royal Society of Chemistry",
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Thiosemicarbazone organocatalysis : Tetrahydropyranylation and 2-deoxygalactosylation reactions and kinetics-based mechanistic investigation. / Larsen, Dennis; Langhorn, Line M.; Akselsen, Olivia M.; Nielsen, Bjarne E.; Pittelkow, Michael.

In: Chemical Science, Vol. 8, No. 12, 2017, p. 7978-7982.

Research output: Contribution to journalJournal articleResearchpeer-review

TY - JOUR

T1 - Thiosemicarbazone organocatalysis

T2 - Tetrahydropyranylation and 2-deoxygalactosylation reactions and kinetics-based mechanistic investigation

AU - Larsen, Dennis

AU - Langhorn, Line M.

AU - Akselsen, Olivia M.

AU - Nielsen, Bjarne E.

AU - Pittelkow, Michael

PY - 2017

Y1 - 2017

N2 - The first use of thiosemicarbazone-based organocatalysis was demonstrated on both tetrahydropyranylation and 2-deoxygalactosylation reactions. The organocatalysts were optimised using kinetics-based selection. The best catalyst outperformed previously reported thiourea catalysts for tetrahydropyranylation by 50-fold. Hammett investigations of both the organocatalyst and the substrate indicate an oxyanion hole-like reaction mechanism.

AB - The first use of thiosemicarbazone-based organocatalysis was demonstrated on both tetrahydropyranylation and 2-deoxygalactosylation reactions. The organocatalysts were optimised using kinetics-based selection. The best catalyst outperformed previously reported thiourea catalysts for tetrahydropyranylation by 50-fold. Hammett investigations of both the organocatalyst and the substrate indicate an oxyanion hole-like reaction mechanism.

U2 - 10.1039/c7sc03366d

DO - 10.1039/c7sc03366d

M3 - Journal article

C2 - 29568444

AN - SCOPUS:85034828020

VL - 8

SP - 7978

EP - 7982

JO - Chemical Science

JF - Chemical Science

SN - 2041-6520

IS - 12

ER -