Bis(pentafluorophenyl)borane catalyzed atom-economic formation of alkenyl- and (homo)allyl boronates from dienes and boronic esters

Based on the finding that bis(pentafluorophenyl)borane reacts with dienes at elevated temperatures to alkenyl boranes, contrary to the expected alkyl boranes, we developed a scalable and atom-economic bis(pentafluorophenyl)borane-catalyzed process for the synthesis of alkenyl and (homo)allyl boronat...

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Published inOrganic chemistry frontiers an international journal of organic chemistry Vol. 11; no. 20; pp. 5921 - 5927
Main Authors Wech, Felix, Koch, Niklas, Müller, Tizian, Gellrich, Urs
Format Journal Article
LanguageEnglish
Published London Royal Society of Chemistry 08.10.2024
Subjects
Alkynes
Boranes
Chemical synthesis
Dienes
Esters
High temperature
Hydroboration
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Summary:Based on the finding that bis(pentafluorophenyl)borane reacts with dienes at elevated temperatures to alkenyl boranes, contrary to the expected alkyl boranes, we developed a scalable and atom-economic bis(pentafluorophenyl)borane-catalyzed process for the synthesis of alkenyl and (homo)allyl boronates from dienes and boronic esters. This method enables the synthesis of cyclic alkenyl boronates with normal ring size that were previously inaccessible via the catalyzed hydroboration of alkynes.
ISSN:2052-4110
2052-4110
DOI:10.1039/d4qo01215a