Intermolecular Pauson–Khand reactions of N-substituted maleimides

Christi Anna L. Brantley; Thomas C. Coombs

doi:10.1016/j.tetlet.2017.10.042

Intermolecular Pauson–Khand reactions of N-substituted maleimides

Christi Anna L. Brantley, Thomas C. Coombs

Isotope Applications Research

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

2 Scopus citations

Abstract

Co₂(CO)₈-mediated intermolecular Pauson–Khand reactions of N-substituted maleimides with terminal alkynes are described, producing maleimide-fused cyclopentenones. The transformation differs from other intermolecular Pauson–Khand-type reactions of electron-deficient olefins, which react with Co₂(CO)₈ and alkynes to produce conjugated dienes, or generally require terminal, monosubstituted olefins to generate cyclopentenones. The reaction works well for N-benzyl, N-aryl, and N-alkyl substituted maleimides, and tolerates branching at the 3-position of the terminal alkyne. N–H maleimide, N–CO₂Me maleimide, and maleic anhydride do not take part in the transformation.

Original language	English
Pages (from-to)	4519-4524
Number of pages	6
Journal	Tetrahedron Letters
Volume	58
Issue number	48
DOIs	https://doi.org/10.1016/j.tetlet.2017.10.042
State	Published - Nov 29 2017

Funding

Acknowledgment is made to the Donors of the American Chemical Society Petroleum Research Fund for support of this research. The NSF Division of Chemistry provided grants through the Major Research Instrumentation Program for mass spectrometry (CHE-1039784) and 600 MHz NMR facilities (CHE-0821552) in the UNC Wilmington Department of Chemistry and Biochemistry. The authors also thank UNC Wilmington for start-up funds. A

Keywords

Cobalt carbonyl
Cyclopentenone
Dicobalt octacarbonyl
Maleimide
Pauson–Khand reaction

Access to Document

10.1016/j.tetlet.2017.10.042

Cite this

@article{f283869fc4e84ad0ae330a3482d3c77c,

title = "Intermolecular Pauson–Khand reactions of N-substituted maleimides",

abstract = "Co2(CO)8-mediated intermolecular Pauson–Khand reactions of N-substituted maleimides with terminal alkynes are described, producing maleimide-fused cyclopentenones. The transformation differs from other intermolecular Pauson–Khand-type reactions of electron-deficient olefins, which react with Co2(CO)8 and alkynes to produce conjugated dienes, or generally require terminal, monosubstituted olefins to generate cyclopentenones. The reaction works well for N-benzyl, N-aryl, and N-alkyl substituted maleimides, and tolerates branching at the 3-position of the terminal alkyne. N–H maleimide, N–CO2Me maleimide, and maleic anhydride do not take part in the transformation.",

keywords = "Cobalt carbonyl, Cyclopentenone, Dicobalt octacarbonyl, Maleimide, Pauson–Khand reaction",

author = "Brantley, \{Christi Anna L.\} and Coombs, \{Thomas C.\}",

note = "Publisher Copyright: {\textcopyright} 2017 Elsevier Ltd",

year = "2017",

month = nov,

day = "29",

doi = "10.1016/j.tetlet.2017.10.042",

language = "English",

volume = "58",

pages = "4519--4524",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier",

number = "48",

}

TY - JOUR

T1 - Intermolecular Pauson–Khand reactions of N-substituted maleimides

AU - Brantley, Christi Anna L.

AU - Coombs, Thomas C.

PY - 2017/11/29

Y1 - 2017/11/29

N2 - Co2(CO)8-mediated intermolecular Pauson–Khand reactions of N-substituted maleimides with terminal alkynes are described, producing maleimide-fused cyclopentenones. The transformation differs from other intermolecular Pauson–Khand-type reactions of electron-deficient olefins, which react with Co2(CO)8 and alkynes to produce conjugated dienes, or generally require terminal, monosubstituted olefins to generate cyclopentenones. The reaction works well for N-benzyl, N-aryl, and N-alkyl substituted maleimides, and tolerates branching at the 3-position of the terminal alkyne. N–H maleimide, N–CO2Me maleimide, and maleic anhydride do not take part in the transformation.

AB - Co2(CO)8-mediated intermolecular Pauson–Khand reactions of N-substituted maleimides with terminal alkynes are described, producing maleimide-fused cyclopentenones. The transformation differs from other intermolecular Pauson–Khand-type reactions of electron-deficient olefins, which react with Co2(CO)8 and alkynes to produce conjugated dienes, or generally require terminal, monosubstituted olefins to generate cyclopentenones. The reaction works well for N-benzyl, N-aryl, and N-alkyl substituted maleimides, and tolerates branching at the 3-position of the terminal alkyne. N–H maleimide, N–CO2Me maleimide, and maleic anhydride do not take part in the transformation.

KW - Cobalt carbonyl

KW - Cyclopentenone

KW - Dicobalt octacarbonyl

KW - Maleimide

KW - Pauson–Khand reaction

UR - https://www.scopus.com/pages/publications/85032201239

U2 - 10.1016/j.tetlet.2017.10.042

DO - 10.1016/j.tetlet.2017.10.042

M3 - Article

AN - SCOPUS:85032201239

SN - 0040-4039

VL - 58

SP - 4519

EP - 4524

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 48

ER -

Intermolecular Pauson–Khand reactions of N-substituted maleimides

Abstract

Funding

Keywords

Access to Document

Other files and links

Fingerprint

Cite this