A one-pot tandem chemoselective allylation/cross-coupling via temperature control of a multi-nucleophile/electrophile system

Chao Xu, James W.B. Fyfe, Ciaran P. Seath, Steven H. Bennett, Allan J.B. Watson

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

A chemoselective tandem reaction of a multi-reactive, two electrophile + two nucleophile, system is reported. An allylation/cross-coupling process of a haloaryl aldehyde, an aryl BPin, and an allyl BPin can be controlled using a temperature gradient to overcome natural reactivity profiles and allow two sequential chemoselective C–C bond formations without intervention. This process offers efficient access to an array of functionalised products including pharmaceutical and natural product scaffolds.
LanguageEnglish
Pages9139-9142
Number of pages4
JournalChemical Communications (London)
Volume53
DOIs
Publication statusPublished - 26 Jul 2017

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Allylation
Nucleophiles
Biological Products
Temperature control
Aldehydes
Scaffolds
Thermal gradients
Pharmaceutical Preparations

Keywords

  • chemoselective tandem reaction
  • bond formations
  • organoboron compounds

Cite this

Xu, Chao ; Fyfe, James W.B. ; Seath, Ciaran P. ; Bennett, Steven H. ; Watson, Allan J.B. / A one-pot tandem chemoselective allylation/cross-coupling via temperature control of a multi-nucleophile/electrophile system. In: Chemical Communications (London). 2017 ; Vol. 53. pp. 9139-9142.
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A one-pot tandem chemoselective allylation/cross-coupling via temperature control of a multi-nucleophile/electrophile system. / Xu, Chao; Fyfe, James W.B.; Seath, Ciaran P.; Bennett, Steven H.; Watson, Allan J.B.

In: Chemical Communications (London), Vol. 53, 26.07.2017, p. 9139-9142.

Research output: Contribution to journalArticle

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AU - Xu, Chao

AU - Fyfe, James W.B.

AU - Seath, Ciaran P.

AU - Bennett, Steven H.

AU - Watson, Allan J.B.

PY - 2017/7/26

Y1 - 2017/7/26

N2 - A chemoselective tandem reaction of a multi-reactive, two electrophile + two nucleophile, system is reported. An allylation/cross-coupling process of a haloaryl aldehyde, an aryl BPin, and an allyl BPin can be controlled using a temperature gradient to overcome natural reactivity profiles and allow two sequential chemoselective C–C bond formations without intervention. This process offers efficient access to an array of functionalised products including pharmaceutical and natural product scaffolds.

AB - A chemoselective tandem reaction of a multi-reactive, two electrophile + two nucleophile, system is reported. An allylation/cross-coupling process of a haloaryl aldehyde, an aryl BPin, and an allyl BPin can be controlled using a temperature gradient to overcome natural reactivity profiles and allow two sequential chemoselective C–C bond formations without intervention. This process offers efficient access to an array of functionalised products including pharmaceutical and natural product scaffolds.

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KW - bond formations

KW - organoboron compounds

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