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Abstract
Non-oxidative, regioselective, and convergent access to densely functionalized oxazoles is realized in a functional-group tolerant manner using alkynyl thioethers. Sulfur-terminated alkynes provide access to reactivity previously requiring strong donor-substituted alkynes such as ynamides. Sulfur does not act in an analogous donor fashion in this gold-catalyzed reaction, thus leading to complementary regioselective outcomes and addressing the limitations of using ynamides.
| Original language | English |
|---|---|
| Pages (from-to) | 13310–13313 |
| Journal | Angewandte Chemie (International Edition) |
| Volume | 56 |
| Issue number | 43 |
| Early online date | 19 Sept 2017 |
| DOIs | |
| Publication status | Published - 16 Oct 2017 |
Keywords
- Gold
- Schwefel
- Cycloadditionen
- Heterocyclen
- Regioselektivität
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Dive into the research topics of 'Alkynyl Thioethers in Gold-Catalyzed Annulations to form Oxazoles'. Together they form a unique fingerprint.-
Gold(I)-catalyzed synthesis of 3-sulfenyl pyrroles and indoles by a regioselective annulation of alkynyl thioethers
Simm, P., Sekar, P., Richardson, J. & Davies, P., 4 Jun 2021, In: ACS Catalysis. 11, 11, p. 6357–6362 6 p.Research output: Contribution to journal › Letter › peer-review
Open AccessFile127 Downloads (Pure) -
Gold-catalyzed annulations with nucleophilic nitrenoids enabled by heteroatom-substituted alkynes
Davies, P., 27 Oct 2021, (E-pub ahead of print) In: The Chemical Record. 21, 12, p. 3964-3977Research output: Contribution to journal › Article › peer-review
Open AccessFile10 Downloads (Pure) -
Sulfenyl ynamides in gold catalysis: synthesis of oxo‐functionalised 4‐aminoimidazolyl fused compounds by intermolecular annulation reactions
Arce, E. M., Lamont, S. G. & Davies, P. W., 15 Jun 2020, In: Advanced Synthesis & Catalysis. 362, 12, p. 2503-2509 7 p.Research output: Contribution to journal › Article › peer-review
Open AccessFile5 Citations (Scopus)114 Downloads (Pure) -
General Entry into o-,o’-Heteroatom-Linked N-(Hetero)aryl Imidazole Motifs by Gold-Catalysed Formal [3+2]-Dipolar Cycloaddition
Davies, P., Garzon Sanz, M., Martinez Arce, E. & Jannapureddy, R., 18 Apr 2017, (E-pub ahead of print) In: Advanced Synthesis & Catalysis.Research output: Contribution to journal › Article › peer-review
Open AccessFile14 Citations (Scopus)207 Downloads (Pure) -
Efficient and flexible synthesis of highly functionalised 4-aminooxazoles by a gold-catalysed intermolecular formal [3+2]-dipolar cycloaddition
Davies, P., Gillie, A. & Jannapureddy, R., 21 Jan 2016, In: Advanced Synthesis & Catalysis. 358, 2, p. 226-239Research output: Contribution to journal › Article › peer-review
Open Access53 Citations (Scopus) -
Nucleophilic nitrenoids through π-acid catalysis: providing a common basis for rapid access into diverse nitrogen heterocycles
Davies, P. & Garzon Sanz, M., Aug 2015, In: Asian Journal of Organic Chemistry. 4, 8, p. 694-708 15 p.Research output: Contribution to journal › Review article › peer-review
Open AccessFile76 Citations (Scopus)241 Downloads (Pure) -
Highly regioselective synthesis of 2,4,5-(hetero)aryl substituted oxazoles by intermolecular [3+2]-cycloaddition of unsymmetrical internal alkynes
Chatzopoulou, E. & Davies, P. W., 7 Oct 2013, In: Chemical Communications . 49, 77, p. 8617-8619 3 p.Research output: Contribution to journal › Article › peer-review
62 Citations (Scopus)
Projects
- 1 Finished
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FP7 MC IIF: SynHet - Convergent and Efficient Synthesis of Novel Heteroaromatics
21/01/13 → 20/01/15
Project: EU
Equipment
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Birmingham Environment for Academic Research (BEAR)
Facility/equipment: Equipment