Synthesis of Highly Functionalized Bismacycles via Post-Transmetallation Modification of Arylboronic Acids

Bismacycles featuring a sulfone-bridged scaffold have recently been developed as versatile and convenient electrophilic arylating agents. Here, we report that the exocyclic aryl group, which is ultimately transferred to a nucleophilic coupling partner, can be functionalized through cross-coupling, h...

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Published inJournal of organic chemistry Vol. 88; no. 14; pp. 9730 - 9736
Main Authors Sivanandan, Sudheesh T., Owen, Benjamin, Guiry, Patrick J., Ball, Liam T.
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 21.07.2023
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
PHENYLATION
DICHLORIDES
OXIDIZING ABILITY
ARYLATION
PENTAVALENT ORGANOBISMUTH REAGENTS
DIARYLIODONIUM SALTS
BISMUTH
SELECTIVITY
TRIARYLBISMUTHANES
ORGANOLEAD
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Summary:Bismacycles featuring a sulfone-bridged scaffold have recently been developed as versatile and convenient electrophilic arylating agents. Here, we report that the exocyclic aryl group, which is ultimately transferred to a nucleophilic coupling partner, can be functionalized through cross-coupling, heteroatom substitutions, oxidations and reductions, and protecting group manipulations. This “postsynthetic modification” approach provides concise and divergent access to complex aryl bismacycles. The utility of the functionalized bismacycles in electrophilic arylation of C–H and O–H bonds is demonstrated.
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ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.3c00361