1,2-Diamination of Alkenes via 1,3-Dipolar Cycloaddition with Azidium Ions or Azides

Setareh Saryazdi; Sean Parkin; Robert B. Grossman

doi:10.1021/acs.orglett.2c03908

1,2-Diamination of Alkenes via 1,3-Dipolar Cycloaddition with Azidium Ions or Azides

Setareh Saryazdi, Sean Parkin, Robert B. Grossman

Chemistry

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

2 Scopus citations

Abstract

We describe two new methods for the 1,2-diamination of alkenes. First, either an azidium ion (ArN═N⁺═NAr) undergoes 1,3-dipolar cycloaddition with an alkene to give a 1,2,3-triazolinium ion directly, or an intramolecular azide-alkene cycloaddition followed by N-benzylation provides the same. Second, hydrogenation of the 1,2,3-triazolinium ion over Raney Ni excises the central N atom and gives the 1,2-diamine. The stereochemistry of the alkene is usually, but not always, preserved in the 1,2-diamine.

Original language	English
Pages (from-to)	331-335
Number of pages	5
Journal	Organic Letters
Volume	25
Issue number	2
DOIs	https://doi.org/10.1021/acs.orglett.2c03908
State	Published - Jan 20 2023

Bibliographical note

Funding Information:
S.S. thanks the University of Kentucky (UK) Department of Chemistry for two RCTF fellowships. The authors thank Prof. Steven Van Lanen and Hoda Saghaian (UK Department of Pharmaceutical Sciences) for allowing us to use their LC-MS instrument.

Publisher Copyright:
© 2023 American Chemical Society.

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.2c03908

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abstract = "We describe two new methods for the 1,2-diamination of alkenes. First, either an azidium ion (ArN═N+═NAr) undergoes 1,3-dipolar cycloaddition with an alkene to give a 1,2,3-triazolinium ion directly, or an intramolecular azide-alkene cycloaddition followed by N-benzylation provides the same. Second, hydrogenation of the 1,2,3-triazolinium ion over Raney Ni excises the central N atom and gives the 1,2-diamine. The stereochemistry of the alkene is usually, but not always, preserved in the 1,2-diamine.",

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T1 - 1,2-Diamination of Alkenes via 1,3-Dipolar Cycloaddition with Azidium Ions or Azides

AU - Saryazdi, Setareh

AU - Parkin, Sean

AU - Grossman, Robert B.

N1 - Funding Information: S.S. thanks the University of Kentucky (UK) Department of Chemistry for two RCTF fellowships. The authors thank Prof. Steven Van Lanen and Hoda Saghaian (UK Department of Pharmaceutical Sciences) for allowing us to use their LC-MS instrument. Publisher Copyright: © 2023 American Chemical Society.

PY - 2023/1/20

Y1 - 2023/1/20

N2 - We describe two new methods for the 1,2-diamination of alkenes. First, either an azidium ion (ArN═N+═NAr) undergoes 1,3-dipolar cycloaddition with an alkene to give a 1,2,3-triazolinium ion directly, or an intramolecular azide-alkene cycloaddition followed by N-benzylation provides the same. Second, hydrogenation of the 1,2,3-triazolinium ion over Raney Ni excises the central N atom and gives the 1,2-diamine. The stereochemistry of the alkene is usually, but not always, preserved in the 1,2-diamine.

AB - We describe two new methods for the 1,2-diamination of alkenes. First, either an azidium ion (ArN═N+═NAr) undergoes 1,3-dipolar cycloaddition with an alkene to give a 1,2,3-triazolinium ion directly, or an intramolecular azide-alkene cycloaddition followed by N-benzylation provides the same. Second, hydrogenation of the 1,2,3-triazolinium ion over Raney Ni excises the central N atom and gives the 1,2-diamine. The stereochemistry of the alkene is usually, but not always, preserved in the 1,2-diamine.

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1,2-Diamination of Alkenes via 1,3-Dipolar Cycloaddition with Azidium Ions or Azides

Abstract

Bibliographical note

ASJC Scopus subject areas

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