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A one-pot synthesis-functionalization strategy for streamlined access to 2,5-disubstituted 1,3, 4-oxadiazoles from carboxylic acids

Abstract:

A one-pot 1,3,4-oxadiazole synthesis-arylation strategy for accessing 2,5-disubstituted 1,3,4-oxadiazoles, from carboxylic acids, N-isocyaniminotriphenylphosphorane (NIITP), and aryl iodides, is reported. The reaction sequence, featuring a second stage copper-catalyzed 1,3,4-oxadiazole arylation, was found to tolerate (hetero)aryl, alkyl, and alkenyl carboxylic acids, and (hetero)aryl iodide coupling partners. The effectiveness of the two-stage strategy was exemplified by the...

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Publication status:
Published
Peer review status:
Peer reviewed

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Publisher copy:
10.1021/acs.joc.2c01669

Authors


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Role:
Author
ORCID:
0000-0002-3340-0049
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Institution:
University of Oxford
Division:
MPLS
Department:
Chemistry
Sub department:
Organic Chemistry
Oxford college:
Wadham College
Role:
Author
ORCID:
0000-0003-2456-5236
Publisher:
American Chemical Society
Journal:
Journal of Organic Chemistry More from this journal
Volume:
87
Issue:
18
Pages:
12498-12505
Publication date:
2022-09-02
Acceptance date:
2022-09-02
DOI:
EISSN:
1520-6904
ISSN:
0022-3263
Pmid:
36054913
Language:
English
Keywords:
Pubs id:
1278258
Local pid:
pubs:1278258
Deposit date:
2023-10-03

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