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Literature DB >> 20462239

Access to 2,5-diamidopyrroles and 2,5-diamidofurans by au(i)-catalyzed double hydroamination or hydration of 1,3-diynes.

Søren Kramer¹, Julie L H Madsen, Mario Rottländer, Troels Skrydstrup.

Abstract

A Au(I)-catalyzed hydroamination or hydration of 1,3-diynes to access 2,5-diamidopyrroles and 2,5-diamidofurans has been developed. This method can also be expanded to 2,5-disubstituted furans and 1,2,5-trisubstituted pyrroles including the formation of deuterated heterocycles and (18)O-labeled furans.

Entities: Chemical

Mesh：

Substances：
Diynes
Furans
Pyrroles
Gold

Year: 2010 PMID： 20462239 DOI： 10.1021/ol1008685

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

Keyword Cloud
Cited

9 in total

1. An Efficient Synthesis of de novo Imidates via Aza-Claisen Rearrangements of N-Allyl Ynamides.

Authors: Kyle A Dekorver; Troy D North; Richard P Hsung
Journal: Synlett Date: 2010-10 Impact factor: 2.454

Review 2. Transition metal-mediated synthesis of monocyclic aromatic heterocycles.

Authors: Anton V Gulevich; Alexander S Dudnik; Natalia Chernyak; Vladimir Gevorgyan
Journal: Chem Rev Date: 2013-01-10 Impact factor: 60.622

3. N-allyl-N-sulfonyl ynamides as synthetic precursors to amidines and vinylogous amidines. An unexpected N-to-C 1,3-sulfonyl shift in nitrile synthesis.

Authors: Kyle A DeKorver; Whitney L Johnson; Yu Zhang; Richard P Hsung; Huifang Dai; Jun Deng; Andrew G Lohse; Yan-Shi Zhang
Journal: J Org Chem Date: 2011-05-24 Impact factor: 4.354

9. Rapid pseudo five-component synthesis of intensively blue luminescent 2,5-di(hetero)arylfurans via a Sonogashira-Glaser cyclization sequence.

Authors: Fabian Klukas; Alexander Grunwald; Franziska Menschel; Thomas J J Müller
Journal: Beilstein J Org Chem Date: 2014-03-18 Impact factor: 2.883

9 in total

Access to 2,5-diamidopyrroles and 2,5-diamidofurans by au(i)-catalyzed double hydroamination or hydration of 1,3-diynes.

1. An Efficient Synthesis of de novo Imidates via Aza-Claisen Rearrangements of N-Allyl Ynamides.

Review 2. Transition metal-mediated synthesis of monocyclic aromatic heterocycles.

3. N-allyl-N-sulfonyl ynamides as synthetic precursors to amidines and vinylogous amidines. An unexpected N-to-C 1,3-sulfonyl shift in nitrile synthesis.

4. Copper-catalyzed Ficini [2 + 2] cycloaddition of ynamides.

5. Ynamides in ring forming transformations.

6. Gold(I)-catalyzed formation of furans by a Claisen-type rearrangement of ynenyl allyl ethers.

7. Simple two-step synthesis of 2,4-disubstituted pyrroles and 3,5-disubstituted pyrrole-2-carbonitriles from enones.

8. Gold(I)-catalyzed formation of furans from γ-acyloxyalkynyl ketones.

9. Rapid pseudo five-component synthesis of intensively blue luminescent 2,5-di(hetero)arylfurans via a Sonogashira-Glaser cyclization sequence.