Sulfur Heterocycles

We have developed a number of new catalysis-based methods for the formation or selective elaboration of sulfur heterocycles from alkyne precursors. See below for some examples, and the following publications.

Gold-catalysed cycloisomerisation of ynamides to access 2,2-disubstituted tetrahydrothiophene motifs, P. Heer Kaur and P. W. Davies* Synlett, 2021, 32, 897-900.

Gold-Catalyzed Intermolecular Alkyne Oxyarylation for C3-Functionalization of Benzothiophenes, P. A. Rist, R. S. Grainger* and P. W. Davies*, Org. Lett. 2021, 23, 642–646.

Synthesis of Thiomorpholin‐3‐ones by a Gold‐Catalysed Oxidative Cyclisation‐Rearrangement Cascade from Ynamides, T. E. Baker, P. W. Davies,* Eur. J. Org. Chem. 2019,  31-32, 5201-5204.

Alkynyl sulfoxides as α-sulfinyl carbene equivalents: Gold-catalysed oxidative cyclopropanation, M. J. Barrett,  G. F. Khan, P. W. Davies,*  R. S. Grainger* Chem. Commun. 2017, 53, 5733-5736.

Regioselective functionalisation of dibenzothiophenes through gold-catalysed intermolecular alkyne oxyarylation, M. J. Barrett, P. W. Davies,* R. S. Grainger,* Org. Biomol. Chem. 2015, 13, 8676-8686.

Gold or Platinum-Catalysed Synthesis of Sulfur Heterocycles: Access to Sulfur Ylides Without Using Sacrificial Functionality; P. W. Davies,* S. J. C. Albrecht, Angew. Chem. Int. Ed. 2009, 48, 8372-8375.

A chemdraw diagram showing the reaction and examples discussed in Org. Lett. 2021 10.1021/acs.orglett.0c03596
C-3 selective benzothiophene modifications
A chemdraw diagram showing the reactions contained in Eur. J. Org. chem. 2019, 31-31, 5201.
An intermolecular oxidation, sulfur ylide formation and rearrangement cascade
chemdrw diagram showing the reaction and examples from Angew. Chem. Int. ed. 2009, 48, 8372
Sulfur heterocycles from cycloisomerisation – replacing diazo groups with alkynes
A chemdraw diagram summarising the transformation of ynamides into tetrahydrothiophenes by an oxidation, ylide formation and rearrangement process catalysed by gold.
Using ynamides to control the cyclisation mode and access tetrahyrothiophenes