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Catalytic Functionalization of Styrenyl Epoxides via 2‐Nickela(II)oxetanes
Author(s) -
Desnoyer Addison N.,
Geng Jialing,
Drover Marcus W.,
Patrick Brian O.,
Love Jennifer A.
Publication year - 2017
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201702824
Subject(s) - hydroboration , isomerization , chemistry , aldehyde , catalysis , surface modification , organic chemistry
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.