Issue 24, 2022
From the journal:

Organic Chemistry Frontiers

Formal insertion of selenoketenes into donor–acceptor cyclopropanes: mesomeric alkynylselenolates as key starting materials†

Anu Jacob,a   Peter G. Jonesb  and  Daniel B. Werz ORCID logo *c  

* Corresponding authors

a Technische Universität Braunschweig, Institute of Organic Chemistry, Hagenring 30, 38106 Braunschweig, Germany

b Technische Universität Braunschweig, Institute of Inorganic and Analytical Chemistry, Hagenring 30, 38106 Braunschweig, Germany

c Albert-Ludwigs-Universität Freiburg, Institute of Organic Chemistry, Albertstraße 21, 79104 Freiburg, Germany
E-mail: daniel.werz@chemie.uni-freiburg.de

Abstract

Donor–acceptor cyclopropanes (DACs) react with lithium alkynylselenolates in the presence of In(OTf)3 to furnish tetrahydroselenophenes with exocyclic double bonds. The reaction can be regarded as a formal insertion of selenoketenes into the strained three-membered ring systems. Lithium alkynylselenolates are generated in situ from lithium acetylides and elemental selenium. The reactions afford tetrahydroselenophenes with a broad substrate scope and high yields (up to 95%).

Graphical abstract: Formal insertion of selenoketenes into donor–acceptor cyclopropanes: mesomeric alkynylselenolates as key starting materials

About
Cited by
Related
Download options Please wait...

Supplementary files

Article information

DOI
https://doi.org/10.1039/D2QO01568D
Article type
Research Article
Submitted
05 Oct 2022
Accepted
07 Nov 2022
First published
07 Nov 2022
This article is Open Access
Creative Commons BY-NC license

Org. Chem. Front., 2022,9, 6933-6939

Permissions

Request permissions

Formal insertion of selenoketenes into donor–acceptor cyclopropanes: mesomeric alkynylselenolates as key starting materials

A. Jacob, P. G. Jones and D. B. Werz, Org. Chem. Front., 2022, 9, 6933 DOI: 10.1039/D2QO01568D

This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence. You can use material from this article in other publications, without requesting further permission from the RSC, provided that the correct acknowledgement is given and it is not used for commercial purposes.

To request permission to reproduce material from this article in a commercial publication, 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 commercial 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