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

doi:10.1039/C7CC05416E

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

School of Chemistry

Research output: Contribution to journal › Article › peer-review

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.

Original language	English
Pages (from-to)	9139-9142
Number of pages	4
Journal	Chemical Communications
Volume	53
Issue number	65
Early online date	26 Jul 2017
DOIs	https://doi.org/10.1039/C7CC05416E
Publication status	Published - 21 Aug 2017

Keywords

Chemoselective tandem reaction
Bond formations
Organoboron compounds

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10.1039/C7CC05416E

https://strathprints.strath.ac.uk/id/eprint/61783

Cite this

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

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.",

keywords = "Chemoselective tandem reaction, Bond formations, Organoboron compounds",

author = "Chao Xu and Fyfe, {James W.B.} and Seath, {Ciaran P.} and Bennett, {Steven H.} and Watson, {Allan J. B.}",

note = "C. X. gratefully acknowledges the Leverhulme Trust for a postdoctoral fellowship (RPG-2015-308). C. P. S. thanks the Carnegie Trust for the Universities of Scotland for a PhD studentship. We thank the University of Strathclyde for funding.",

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doi = "10.1039/C7CC05416E",

language = "English",

volume = "53",

pages = "9139--9142",

journal = "Chemical Communications",

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publisher = "Royal Society of Chemistry",

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T1 - A one-pot tandem chemoselective allylation/cross-coupling via temperature control of a multi-nucleophile/electrophile system

AU - Xu, Chao

AU - Fyfe, James W.B.

AU - Seath, Ciaran P.

AU - Bennett, Steven H.

AU - Watson, Allan J. B.

N1 - C. X. gratefully acknowledges the Leverhulme Trust for a postdoctoral fellowship (RPG-2015-308). C. P. S. thanks the Carnegie Trust for the Universities of Scotland for a PhD studentship. We thank the University of Strathclyde for funding.

PY - 2017/8/21

Y1 - 2017/8/21

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.

KW - Chemoselective tandem reaction

KW - Bond formations

KW - Organoboron compounds

U2 - 10.1039/C7CC05416E

DO - 10.1039/C7CC05416E

M3 - Article

SN - 1359-7345

VL - 53

SP - 9139

EP - 9142

JO - Chemical Communications

JF - Chemical Communications

IS - 65

ER -

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

Abstract

Keywords

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