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Conversion of Alkyl Azides to Diazo Compounds and the Azide-Site Selectivity: One-Pot Phosphine-Mediated Transient Protection of Azido Groups and Deprotective Transformation to Diazo Groups

09 February 2024, Version 1
Working Paper
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

A one-pot conversion of alkyl azides to diazo compounds is outlined. After azido group protection of α-azidocarbonyl compounds, treatment of the resulting phosphazides with silica gel in a wet solvent afforded α-diazo carbonyl products by azide-deprotective conversion. Competitive reactions of α-azido amides with alkyl and aryl azides demonstrate azide-site selectivity. Azide-site selective click functionalization by this one-pot sequence is also demonstrated with diazido compounds.

Keywords

Organic Azides
Diazo Compounds
Phosphines
Protecting Groups
Click Chemistry

Supplementary materials

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Description
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Supporting Information
Description
This file contains the experimental procedures and analytical data (1H, 13C NMR, IR, mass spectroscopy, melting point, and Rf values) of the compounds, including NMR and MS studies.
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Now Published

Amphos-Mediated Conversion of Alkyl Azides to Diazo Compounds and One-Pot Azide-Site Selective Transient Protection, Click Conjugation, and Deprotective Transformation [opens in a new tab]
Hiroki Tanimoto, Ryo Adachi, Kodai Tanisawa, Takenori Tomohiro journal article
Organic Letters , Volume 26, Issue 12
Online publication date: Mar 19, 2024

Version History

Feb 09, 2024 Version 1

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The content is available under CC BY NC ND 4.0 [opens in a new tab]

DOI

10.26434/chemrxiv-2024-37p57
D O I: 10.26434/chemrxiv-2024-37p57 [opens in a new tab]

Funding

Japan Society for the Promotion of Science
JP22K06523
JGC-S (Nikki-Saneyoshi) Scholarship Foundation
2119
Takeda Science Foundation
Iketani Science and Technology Foundation
0351145-A

Author’s competing interest statement

The author(s) have declared they have no conflict of interest with regard to this content

Ethics

The author(s) have declared ethics committee/IRB approval is not relevant to this content

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