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Literature DB >> 17288372

Au-catalyzed reaction of propargylic sulfides and dithioacetals.

Lingling Peng¹, Xiu Zhang, Shiwei Zhang, Jianbo Wang.

Abstract

Propargylic sulfides and dithioacetals are found to undergo similar transformations as propargylic carboxylates when catalyzed by AuCl or AuCl3, affording indene derivatives through pentannulation of aromatic rings. The reaction presumably involves Au carbene as the reactive intermediate.

Entities: Chemical

Year: 2007 PMID： 17288372 DOI： 10.1021/jo0618674

Source DB: PubMed Journal: J Org Chem ISSN： 0022-3263 Impact factor: 4.354

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Cited

8 in total

1. Copper-, Silver-, and Gold-Catalyzed Migratory Cycloisomerizations Leading to Heterocyclic Five-Membered Rings.

Authors: Alexander S Dudnik; Natalia Chernyak; Vladimir Gevorgyan
Journal: Aldrichimica Acta Date: 2010 Impact factor: 3.667

2. Sulfur Transfer Versus Phenyl Ring Transfer in the Gas Phase: Sequential Loss of CH₃OH and CH₃O-P=O from Protonated Phosphorothioates.

Authors: Xiaoping Zhang; Honghan Chen; Yin Ji; Kezhi Jiang; Huanwen Chen
Journal: J Am Soc Mass Spectrom Date: 2018-12-19 Impact factor: 3.109

3. Silylene transfer to allylic sulfides: formation of substituted silacyclobutanes.

Authors: Bryan J Ager; Laura E Bourque; Kay M Buchner; K A Woerpel
Journal: J Org Chem Date: 2010-08-20 Impact factor: 4.354

4. Metal-catalyzed 1,2-shift of diverse migrating groups in allenyl systems as a new paradigm toward densely functionalized heterocycles.

Authors: Alexander S Dudnik; Anna W Sromek; Marina Rubina; Joseph T Kim; Alexander V Kel'in; Vladimir Gevorgyan
Journal: J Am Chem Soc Date: 2008-01-04 Impact factor: 15.419

5. Mechanistically diverse copper-, silver-, and gold-catalyzed acyloxy and phosphatyloxy migrations: efficient synthesis of heterocycles via cascade migration/cycloisomerization approach.

Authors: Todd Schwier; Anna W Sromek; Dahrika M L Yap; Dmitri Chernyak; Vladimir Gevorgyan
Journal: J Am Chem Soc Date: 2007-07-21 Impact factor: 15.419

Au-catalyzed reaction of propargylic sulfides and dithioacetals.

1. Copper-, Silver-, and Gold-Catalyzed Migratory Cycloisomerizations Leading to Heterocyclic Five-Membered Rings.

2. Sulfur Transfer Versus Phenyl Ring Transfer in the Gas Phase: Sequential Loss of CH₃OH and CH₃O-P=O from Protonated Phosphorothioates.

3. Silylene transfer to allylic sulfides: formation of substituted silacyclobutanes.

4. Metal-catalyzed 1,2-shift of diverse migrating groups in allenyl systems as a new paradigm toward densely functionalized heterocycles.

5. Mechanistically diverse copper-, silver-, and gold-catalyzed acyloxy and phosphatyloxy migrations: efficient synthesis of heterocycles via cascade migration/cycloisomerization approach.

6. Solvent- and ligand-induced switch of selectivity in gold(I)-catalyzed tandem reactions of 3-propargylindoles.

7. 2-Meth-oxy-4-methyl-1-[1-(phenyl-sulfon-yl)propan-2-yl]benzene.

8. Gold(I)-catalysed direct thioetherifications using allylic alcohols: an experimental and computational study.