Magnesium-mediated benzothiazole activation

a room temperature cascade of C-H deprotonation, C-C coupling, ring-opening and nucleophilic addition reactions

Victoria L. Blair, William Clegg, Alan R. Kennedy, Zoe Livingstone, Luca Russo, Eva Hevia

Research output: Contribution to journalArticle

24 Citations (Scopus)

Abstract

Ligand domin(o)ated: In contrast to the straightforward deprotonation of benzothiazole using Grignard reagents, treatment of benzothiazole with 1 leads to a novel type of activation. The initial magnesiation initiates an unstoppable domino reaction of CC coupling, ring opening, nucleophilic addition, and deprotonation to give 2. THF=tetrahydrofuran.
Original languageEnglish
Pages (from-to)9857-9860
Number of pages4
JournalAngewandte Chemie
Volume50
Issue number42
DOIs
Publication statusPublished - 10 Oct 2011

Fingerprint

Magnesium
Temperature
Ligands
benzothiazole
tetrahydrofuran

Keywords

  • cascade reactions
  • heterocylces
  • magnesium
  • metalation
  • mixed-metal chemistry

Cite this

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abstract = "Ligand domin(o)ated: In contrast to the straightforward deprotonation of benzothiazole using Grignard reagents, treatment of benzothiazole with 1 leads to a novel type of activation. The initial magnesiation initiates an unstoppable domino reaction of CC coupling, ring opening, nucleophilic addition, and deprotonation to give 2. THF=tetrahydrofuran.",
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Magnesium-mediated benzothiazole activation : a room temperature cascade of C-H deprotonation, C-C coupling, ring-opening and nucleophilic addition reactions. / Blair, Victoria L.; Clegg, William; Kennedy, Alan R.; Livingstone, Zoe; Russo, Luca; Hevia, Eva.

In: Angewandte Chemie, Vol. 50, No. 42, 10.10.2011, p. 9857-9860.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Magnesium-mediated benzothiazole activation

T2 - a room temperature cascade of C-H deprotonation, C-C coupling, ring-opening and nucleophilic addition reactions

AU - Blair, Victoria L.

AU - Clegg, William

AU - Kennedy, Alan R.

AU - Livingstone, Zoe

AU - Russo, Luca

AU - Hevia, Eva

PY - 2011/10/10

Y1 - 2011/10/10

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AB - Ligand domin(o)ated: In contrast to the straightforward deprotonation of benzothiazole using Grignard reagents, treatment of benzothiazole with 1 leads to a novel type of activation. The initial magnesiation initiates an unstoppable domino reaction of CC coupling, ring opening, nucleophilic addition, and deprotonation to give 2. THF=tetrahydrofuran.

KW - cascade reactions

KW - heterocylces

KW - magnesium

KW - metalation

KW - mixed-metal chemistry

U2 - 10.1002/anie.201103275

DO - 10.1002/anie.201103275

M3 - Article

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EP - 9860

JO - Angewandte Chemie International Edition

JF - Angewandte Chemie International Edition

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