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Catalytic Functionalization of Styrenyl Epoxides via 2-Nickela(II)oxetanes

TitleCatalytic Functionalization of Styrenyl Epoxides via 2-Nickela(II)oxetanes
Publication TypeJournal Article
Year of Publication2017
AuthorsDesnoyer, AN, Geng, J, Drover, MW, Patrick, BO, Love, JA
JournalCHEMISTRY-A EUROPEAN JOURNAL
Volume23
Pagination11509-11512
Date PublishedAUG 25
ISSN0947-6539
Abstract

Low-valent nickel is shown to preferentially isomerize mono-or disubstituted epoxides into their corresponding aldehydes. Experiments with tetrasubstituted epoxides demonstrate that these reactions proceed via reactive 2-nickelaoxetane intermediates, and that the oxidative addition step likely occurs with retention of configuration. The monosubstituted aldehyde isomerization products were found to rapidly react with HBpin to form boronate esters. These hydroboration reactions could be performed catalytically.

DOI10.1002/chem.201702824