Strategy for conditional orthogonal sequential CuAAC reactions using a protected aromatic ynamine

Marine Z. C. Hatit; Ciaran P. Seath; Allan J. B. Watson; Glenn A. Burley

doi:10.1021/acs.joc.7b00545

Strategy for conditional orthogonal sequential CuAAC reactions using a protected aromatic ynamine

Marine Z. C. Hatit, Ciaran P. Seath, Allan J. B. Watson, Glenn A. Burley

School of Chemistry

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

Abstract

A method for conditional control of orthogonal sequential Cu-catalyzed azide alkyne cycloaddition (CuAAC) reactions is reported. The inherent reactivity of an aromatic ynamine is controlled by a silyl protecting group that allows the selective CuAAC reaction of less reactive alkynes. Alternatively, the same protected ynamine undergoes selective CuAAC reaction via silyl deprotection in situ to give theynamine click products. This allows complete orthogonal control of dialkyne systems and provides a unifying strategy for chemoselective CuAAC ligations in multi-alkyne/azide systems.

Original language	English
Pages (from-to)	5461-5468
Journal	The Journal of Organic Chemistry
Volume	82
Issue number	10
Early online date	28 Apr 2017
DOIs	https://doi.org/10.1021/acs.joc.7b00545
Publication status	Published - 19 May 2017

Keywords

Cu-catalyzed azide alkyne cycloaddition
Aromatic ynamine
Silyl deprotection

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10.1021/acs.joc.7b00545

https://strathprints.strath.ac.uk/id/eprint/60572

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title = "Strategy for conditional orthogonal sequential CuAAC reactions using a protected aromatic ynamine",

abstract = "A method for conditional control of orthogonal sequential Cu-catalyzed azide alkyne cycloaddition (CuAAC) reactions is reported. The inherent reactivity of an aromatic ynamine is controlled by a silyl protecting group that allows the selective CuAAC reaction of less reactive alkynes. Alternatively, the same protected ynamine undergoes selective CuAAC reaction via silyl deprotection in situ to give theynamine click products. This allows complete orthogonal control of dialkyne systems and provides a unifying strategy for chemoselective CuAAC ligations in multi-alkyne/azide systems.",

keywords = "Cu-catalyzed azide alkyne cycloaddition, Aromatic ynamine, Silyl deprotection",

author = "Hatit, {Marine Z. C.} and Seath, {Ciaran P.} and Watson, {Allan J. B.} and Burley, {Glenn A.}",

note = "M.Z.C.H. thanks the University of Strathclyde for a PhD scholarship. C.P.S. thanks the Carnegie Trust for the Universities of Scotland for a PhD scholarship. ",

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doi = "10.1021/acs.joc.7b00545",

language = "English",

volume = "82",

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journal = "The Journal of Organic Chemistry",

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publisher = "American Chemical Society (ACS)",

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T1 - Strategy for conditional orthogonal sequential CuAAC reactions using a protected aromatic ynamine

AU - Hatit, Marine Z. C.

AU - Seath, Ciaran P.

AU - Watson, Allan J. B.

AU - Burley, Glenn A.

N1 - M.Z.C.H. thanks the University of Strathclyde for a PhD scholarship. C.P.S. thanks the Carnegie Trust for the Universities of Scotland for a PhD scholarship.

PY - 2017/5/19

Y1 - 2017/5/19

N2 - A method for conditional control of orthogonal sequential Cu-catalyzed azide alkyne cycloaddition (CuAAC) reactions is reported. The inherent reactivity of an aromatic ynamine is controlled by a silyl protecting group that allows the selective CuAAC reaction of less reactive alkynes. Alternatively, the same protected ynamine undergoes selective CuAAC reaction via silyl deprotection in situ to give theynamine click products. This allows complete orthogonal control of dialkyne systems and provides a unifying strategy for chemoselective CuAAC ligations in multi-alkyne/azide systems.

AB - A method for conditional control of orthogonal sequential Cu-catalyzed azide alkyne cycloaddition (CuAAC) reactions is reported. The inherent reactivity of an aromatic ynamine is controlled by a silyl protecting group that allows the selective CuAAC reaction of less reactive alkynes. Alternatively, the same protected ynamine undergoes selective CuAAC reaction via silyl deprotection in situ to give theynamine click products. This allows complete orthogonal control of dialkyne systems and provides a unifying strategy for chemoselective CuAAC ligations in multi-alkyne/azide systems.

KW - Cu-catalyzed azide alkyne cycloaddition

KW - Aromatic ynamine

KW - Silyl deprotection

U2 - 10.1021/acs.joc.7b00545

DO - 10.1021/acs.joc.7b00545

M3 - Article

SN - 0022-3263

VL - 82

SP - 5461

EP - 5468

JO - The Journal of Organic Chemistry

JF - The Journal of Organic Chemistry

IS - 10

ER -

Strategy for conditional orthogonal sequential CuAAC reactions using a protected aromatic ynamine

Abstract

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