Issue 6, 2010

Functionalized alkoxy arene diazonium salts from paracetamol

Abstract

Arene diazonium tetrafluoroborates can be synthesized from aromatic acetamides via a sequence of deacetylation, diazotation and precipitation, induced by anion exchange. The reaction is conducted as a convenient one-flask transformation with consecutive addition of the appropriate reagents. Exchange of solvents or removal of byproducts prior to isolation of the product is not required. The arene diazonium salts are isolated from the reaction mixture by simple filtration. Two complementary protocols are presented, and the utility of the reaction is exemplified for a synthesis of the diarylheptanoid natural product de-O-methyl centrolobine.

Graphical abstract: Functionalized alkoxy arene diazonium salts from paracetamol

Supplementary files

Article information

Article type
Paper
Submitted
23 Nov 2009
Accepted
17 Dec 2009
First published
19 Jan 2010

Org. Biomol. Chem., 2010,8, 1406-1414

Functionalized alkoxy arene diazonium salts from paracetamol

B. Schmidt, R. Berger and F. Hölter, Org. Biomol. Chem., 2010, 8, 1406 DOI: 10.1039/B924619C

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements