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Copper(I)-catalyzed sulfonylative Suzuki-Miyaura cross-coupling

Abstract:
Using a simple copper(I) catalyst has allowed a high yielding sulfonylative-Suzuki-Miyaura cross-coupling to be developed. The process provides a single step route to diaryl sulfones from the direct combination of aryl boronic acids, sulfur dioxide and aryl iodides, and represents the first sulfonylative variant of a classic cross-coupling reaction. Sulfur dioxide is delivered from the surrogate reagent, DABSO. Variation of the reaction conditions allowed interruption of the sulfonylative-Suzuki coupling, resulting in formation of a presumed Cu-sulfinate intermediate. These sufinates could be trapped with electrophiles to access to arylalkyl sulfones, β-hydroxyl sulfones, sulfonamides and sulfonyl fluorides.
Publication status:
Published
Peer review status:
Peer reviewed

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Publisher copy:
10.1039/c6sc05483h

Authors


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Institution:
University of Oxford
Oxford college:
Lincoln College
Role:
Author
More by this author
Institution:
University of Oxford
Division:
MPLS
Department:
Chemistry
Sub department:
Organic Chemistry
Role:
Author


Publisher:
Royal Society of Chemistry
Journal:
Chemical Science More from this journal
Volume:
8
Issue:
4
Pages:
3249–3253
Publication date:
2017-02-28
Acceptance date:
2017-02-16
DOI:
EISSN:
2041-6539
ISSN:
2041-6520


Pubs id:
pubs:680397
UUID:
uuid:7252901c-1fba-4520-ace1-7dcda651048e
Local pid:
pubs:680397
Source identifiers:
680397
Deposit date:
2017-02-16

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