Issue 7, 2020
From the journal:

Chemical Science

From 1,2-difunctionalisation to cyanide-transfer cascades – Pd-catalysed cyanosulfenylation of internal (oligo)alkynes†

Marcel Bürger, ORCID logo a   Maximilian N. Loch, ORCID logo a   Peter G. Jonesb  and  Daniel B. Werz ORCID logo *a  

* Corresponding authors

a Technische Universität Braunschweig, Institute of Organic Chemistry, Hagenring 30, 38106 Braunschweig, Germany
E-mail: d.werz@tu-braunschweig.de

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

Abstract

Internal alkynes substituted by aliphatic or aromatic moieties or by heteroatoms were converted into sulphur-substituted acrylonitrile derivatives. Key is the use of Pd catalysis, which allows the addition of aromatic and aliphatic thiocyanates in an intra- and intermolecular manner. Substrates with several alkyne units underwent further carbopalladation steps after the initial thiopalladation step, thus generating in a cascade-like fashion an oligoene unit with sulphur at one terminus and the cyano group at the other.

Graphical abstract: From 1,2-difunctionalisation to cyanide-transfer cascades – Pd-catalysed cyanosulfenylation of internal (oligo)alkynes

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Article information

DOI
https://doi.org/10.1039/C9SC04569D
Article type
Edge Article
Submitted
10 Sep 2019
Accepted
22 Dec 2019
First published
23 Dec 2019
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2020,11, 1912-1917

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From 1,2-difunctionalisation to cyanide-transfer cascades – Pd-catalysed cyanosulfenylation of internal (oligo)alkynes

M. Bürger, M. N. Loch, P. G. Jones and D. B. Werz, Chem. Sci., 2020, 11, 1912 DOI: 10.1039/C9SC04569D

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