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Arylsulfonyl fluoride boronic acids: preparation and coupling reactivity

Abstract:
We report the efficient and practical syntheses of ortho-, meta, and para-sulfonyl fluoride substituted benzene boronic acids. The syntheses of the para- and meta-isomers commence with the appropriate bromo-substituted benzenesulfonyl chlorides, and the ortho-isomer is prepared from benzenesulfonyl fluoride. The boronic acids undergo efficient Sukuki-Miyaura coupling reactions with a range of aryl halides. We also report an efficient Rh(I)-catalyzed conjugate addition reaction using the para-substituted boronic acid.
Publication status:
Published
Peer review status:
Peer reviewed

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Publisher copy:
10.1016/j.tet.2019.130782

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Institution:
University of Oxford
Division:
MPLS
Department:
Chemistry
Sub department:
Organic Chemistry
Oxford college:
Lincoln College
Role:
Author
ORCID:
0000-0002-0636-6471


Publisher:
Elsevier
Journal:
Tetrahedron More from this journal
Volume:
76
Issue:
1
Article number:
130782
Publication date:
2019-11-18
Acceptance date:
2019-11-08
DOI:
ISSN:
0040-4020


Language:
English
Keywords:
Pubs id:
pubs:1070542
UUID:
uuid:84e825ab-8db9-4169-b8b7-811ba0396c6b
Local pid:
pubs:1070542
Source identifiers:
1070542
Deposit date:
2019-11-08

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