Iron(II)-mediated nitrene transfer from t-butyloxycarbonyl azide (BocN3) to sulfoxides, sulfides, and ketene acetals

Thorsten Bach; Christina Körber

doi:10.1016/S0040-4039(98)00927-7

Iron(II)-mediated nitrene transfer from t-butyloxycarbonyl azide (BocN₃) to sulfoxides, sulfides, and ketene acetals

Thorsten Bach, Christina Körber

Philipps-Universität Marburg

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

84 Scopus citations

Abstract

The nitrene transfer from t-butyloxycarbonyl azide (BocN₃) to several nucleophiles is promoted by ferrous chloride (FeCl₂) and yields the corresponding N-Boc protected sulfoximides, sulfimides, or α-amino alkanoates. Whereas the sulfoximide formation occurs spontaneously in CH₂Cl₂ as solvent the FeCl₂-catalyzed nitrene transfer to sulfides and ketene acetals requires addition of a polar solvent. DMF was found to be best suited for this purpose.

Original language	English
Pages (from-to)	5015-5016
Number of pages	2
Journal	Tetrahedron Letters
Volume	39
Issue number	28
DOIs	https://doi.org/10.1016/S0040-4039(98)00927-7
State	Published - 9 Jul 1998
Externally published	Yes

Keywords

Catalysis
Nitrenes
Sulfimides
Sulfoximides

Access to Document

10.1016/S0040-4039(98)00927-7

Cite this

@article{49f6731ce0bf492686bb8eea9a1d055f,

title = "Iron(II)-mediated nitrene transfer from t-butyloxycarbonyl azide (BocN3) to sulfoxides, sulfides, and ketene acetals",

abstract = "The nitrene transfer from t-butyloxycarbonyl azide (BocN3) to several nucleophiles is promoted by ferrous chloride (FeCl2) and yields the corresponding N-Boc protected sulfoximides, sulfimides, or α-amino alkanoates. Whereas the sulfoximide formation occurs spontaneously in CH2Cl2 as solvent the FeCl2-catalyzed nitrene transfer to sulfides and ketene acetals requires addition of a polar solvent. DMF was found to be best suited for this purpose.",

keywords = "Catalysis, Nitrenes, Sulfimides, Sulfoximides",

author = "Thorsten Bach and Christina K{\"o}rber",

note = "Funding Information: Acknowledgements. This work was generously supported by the Deutsche Forschungsgemeinschaft (Graduiertenkolleg {\textquoteleft}Metallorganische Chemie{\textquoteright}), and by the Fonds der Chemischen Industrie.",

year = "1998",

month = jul,

day = "9",

doi = "10.1016/S0040-4039(98)00927-7",

language = "English",

volume = "39",

pages = "5015--5016",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Ltd.",

number = "28",

}

TY - JOUR

T1 - Iron(II)-mediated nitrene transfer from t-butyloxycarbonyl azide (BocN3) to sulfoxides, sulfides, and ketene acetals

AU - Bach, Thorsten

AU - Körber, Christina

N1 - Funding Information: Acknowledgements. This work was generously supported by the Deutsche Forschungsgemeinschaft (Graduiertenkolleg ‘Metallorganische Chemie’), and by the Fonds der Chemischen Industrie.

PY - 1998/7/9

Y1 - 1998/7/9

N2 - The nitrene transfer from t-butyloxycarbonyl azide (BocN3) to several nucleophiles is promoted by ferrous chloride (FeCl2) and yields the corresponding N-Boc protected sulfoximides, sulfimides, or α-amino alkanoates. Whereas the sulfoximide formation occurs spontaneously in CH2Cl2 as solvent the FeCl2-catalyzed nitrene transfer to sulfides and ketene acetals requires addition of a polar solvent. DMF was found to be best suited for this purpose.

AB - The nitrene transfer from t-butyloxycarbonyl azide (BocN3) to several nucleophiles is promoted by ferrous chloride (FeCl2) and yields the corresponding N-Boc protected sulfoximides, sulfimides, or α-amino alkanoates. Whereas the sulfoximide formation occurs spontaneously in CH2Cl2 as solvent the FeCl2-catalyzed nitrene transfer to sulfides and ketene acetals requires addition of a polar solvent. DMF was found to be best suited for this purpose.

KW - Catalysis

KW - Nitrenes

KW - Sulfimides

KW - Sulfoximides

UR - http://www.scopus.com/inward/record.url?scp=0032500089&partnerID=8YFLogxK

U2 - 10.1016/S0040-4039(98)00927-7

DO - 10.1016/S0040-4039(98)00927-7

M3 - Article

AN - SCOPUS:0032500089

SN - 0040-4039

VL - 39

SP - 5015

EP - 5016

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 28

ER -

Iron(II)-mediated nitrene transfer from t-butyloxycarbonyl azide (BocN₃) to sulfoxides, sulfides, and ketene acetals

Abstract

Keywords

Access to Document

Other files and links

Fingerprint

Cite this