Synthesis of a rotaxane CuI Triazolide under aqueous conditions
Synthesis of a rotaxane CuI Triazolide under aqueous conditions
We describe the serendipitous isolation of a stable, neutral, monomeric mechanically interlocked CuI triazolide under aqueous conditions. This “trapped” intermediate of the CuAAC catalytic cycle is sterically protected from reprotonation by the rotaxane architecture, which renders the CuI–C bond stable toward moisture and air—even carboxylic acids protonate the CuI–C bond only slowly. The isolation of this remarkably stable CuI organometallic points toward potential applications of mechanical bonding in the study of reactive intermediates.
13318-13321
Winn, Joby
5f38d7c8-e656-4191-85c5-1323197b0bdd
Pinczewska, Aleksandra
dc358574-75de-4ac4-9f30-2b7f3ea151cc
Goldup, Stephen M.
0a93eedd-98bb-42c1-a963-e2815665e937
23 August 2013
Winn, Joby
5f38d7c8-e656-4191-85c5-1323197b0bdd
Pinczewska, Aleksandra
dc358574-75de-4ac4-9f30-2b7f3ea151cc
Goldup, Stephen M.
0a93eedd-98bb-42c1-a963-e2815665e937
Winn, Joby, Pinczewska, Aleksandra and Goldup, Stephen M.
(2013)
Synthesis of a rotaxane CuI Triazolide under aqueous conditions.
Journal of the American Chemical Society, 135 (36), .
(doi:10.1021/ja407446c).
(PMID:23971866)
Abstract
We describe the serendipitous isolation of a stable, neutral, monomeric mechanically interlocked CuI triazolide under aqueous conditions. This “trapped” intermediate of the CuAAC catalytic cycle is sterically protected from reprotonation by the rotaxane architecture, which renders the CuI–C bond stable toward moisture and air—even carboxylic acids protonate the CuI–C bond only slowly. The isolation of this remarkably stable CuI organometallic points toward potential applications of mechanical bonding in the study of reactive intermediates.
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Published date: 23 August 2013
Organisations:
Organic Chemistry: Synthesis, Catalysis and Flow
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Local EPrints ID: 370649
URI: http://eprints.soton.ac.uk/id/eprint/370649
ISSN: 0002-7863
PURE UUID: dff356c3-ccf9-4c4c-80c5-1451f038e6e3
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Date deposited: 03 Nov 2014 12:45
Last modified: 14 Mar 2024 18:19
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Author:
Joby Winn
Author:
Aleksandra Pinczewska
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