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

Addison N. Desnoyer; Jialing Geng; Marcus W. Drover; Brian O. Patrick; Jennifer A. Love

doi:10.1002/chem.201702824

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

Addison N. Desnoyer, Jialing Geng, Marcus W. Drover, Brian O. Patrick, Jennifer A. Love

Chemistry (Twin Cities)

Research output: Contribution to journal › Article › peer-review

31 Scopus citations

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.

Original language	English (US)
Pages (from-to)	11509-11512
Number of pages	4
Journal	Chemistry - A European Journal
Volume	23
Issue number	48
DOIs	https://doi.org/10.1002/chem.201702824
State	Published - Aug 25 2017

Bibliographical note

Publisher Copyright:
© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

Keywords

epoxides
hydroboration
isomerization
metallaheterocycles
nickel

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10.1002/chem.201702824

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title = "Catalytic Functionalization of Styrenyl Epoxides via 2-Nickela(II)oxetanes",

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.",

keywords = "epoxides, hydroboration, isomerization, metallaheterocycles, nickel",

author = "Desnoyer, {Addison N.} and Jialing Geng and Drover, {Marcus W.} and Patrick, {Brian O.} and Love, {Jennifer A.}",

note = "Publisher Copyright: {\textcopyright} 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim",

year = "2017",

month = aug,

day = "25",

doi = "10.1002/chem.201702824",

language = "English (US)",

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T1 - Catalytic Functionalization of Styrenyl Epoxides via 2-Nickela(II)oxetanes

AU - Desnoyer, Addison N.

AU - Geng, Jialing

AU - Drover, Marcus W.

AU - Patrick, Brian O.

AU - Love, Jennifer A.

PY - 2017/8/25

Y1 - 2017/8/25

N2 - 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.

AB - 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.

KW - epoxides

KW - hydroboration

KW - isomerization

KW - metallaheterocycles

KW - nickel

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DO - 10.1002/chem.201702824

M3 - Article

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AN - SCOPUS:85026745216

SN - 0947-6539

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SP - 11509

EP - 11512

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

IS - 48

ER -

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

Abstract

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Keywords

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