Warning: Undefined array key "mm" in /www/wwwroot/www.ai-bt.com/si.php on line 10 Deprecated: trim(): Passing null to parameter #1 ($string) of type string is deprecated in /www/wwwroot/www.ai-bt.com/si.php on line 10 Synthesis of 2,3-disubstituted benzofurans by platinum-olefin-catalyzed carboalkoxylation of o-alkynylphenyl acetals.

Literature DB >> 16248630

Synthesis of 2,3-disubstituted benzofurans by platinum-olefin-catalyzed carboalkoxylation of o-alkynylphenyl acetals.

Itaru Nakamura¹, Yuya Mizushima, Yoshinori Yamamoto.

Abstract

The PtCl2-catalyzed cyclization reaction of o-alkynylphenyl acetals 1 in the presence of 1,5-cyclooctadiene produces 3-(alpha-alkoxyalkyl)benzofurans 2 in good to high yields. For example, the reaction of acetaldehyde ethyl 2-(1-octynyl)phenyl acetal (1a), acetaldehyde ethyl 2-(cyclohexylethynyl)phenyl acetal (1c), and acetaldehyde ethyl 2-(phenylethynyl)phenyl acetal (1f) in the presence of 2 mol % of platinum(II) chloride and 8 mol % of 1,5-cyclooctadiene in toluene at 30 degrees C gave the corresponding 2,3-disubstituted benzofurans 2a, 2c, and 2f in 91, 94, and 88% yields, respectively.

Entities: Chemical

Year: 2005 PMID： 16248630 DOI： 10.1021/ja055202f

Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419

Keyword Cloud
Cited

10 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. Total synthesis of (±)-rocaglamide via oxidation-initiated Nazarov cyclization.

Authors: John A Malona; Kevin Cariou; William T Spencer; Alison J Frontier
Journal: J Org Chem Date: 2012-01-26 Impact factor: 4.354

3. Gold(I)-catalyzed enantioselective carboalkoxylation of alkynes.

Authors: Weiwei Zi; F Dean Toste
Journal: J Am Chem Soc Date: 2013-08-19 Impact factor: 15.419

4. A Reactivity-Driven Approach to the Discovery and Development of Gold-Catalyzed Organic Reactions.

Authors: Nathan D Shapiro; F Dean Toste
Journal: Synlett Date: 2010-03-01 Impact factor: 2.454

5. Gold(I)-catalyzed enantioselective synthesis of benzopyrans via rearrangement of allylic oxonium intermediates.

Authors: Minoru Uemura; Iain D G Watson; Mikimoto Katsukawa; F Dean Toste
Journal: J Am Chem Soc Date: 2009-03-18 Impact factor: 15.419

6. Palladium-Catalyzed Synthesis of 2,3-Disubstituted Benzofurans: An Approach Towards the Synthesis of Deuterium Labeled Compounds.

Authors: Soumitra Agasti; Soham Maity; Kalman J Szabo; Debabrata Maiti
Journal: Adv Synth Catal Date: 2015-07-14 Impact factor: 5.837

Synthesis of 2,3-disubstituted benzofurans by platinum-olefin-catalyzed carboalkoxylation of o-alkynylphenyl acetals.

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

2. Total synthesis of (±)-rocaglamide via oxidation-initiated Nazarov cyclization.

3. Gold(I)-catalyzed enantioselective carboalkoxylation of alkynes.

4. A Reactivity-Driven Approach to the Discovery and Development of Gold-Catalyzed Organic Reactions.

5. Gold(I)-catalyzed enantioselective synthesis of benzopyrans via rearrangement of allylic oxonium intermediates.

6. Palladium-Catalyzed Synthesis of 2,3-Disubstituted Benzofurans: An Approach Towards the Synthesis of Deuterium Labeled Compounds.

7. Direct Arylation of Benzo[b]furan and Other Benzo-Fused Heterocycles.

8. Gold-catalyzed intermolecular coupling of sulfonylacetylene with allyl ethers: [3,3]- and [1,3]-rearrangements.

9. Alkoxyboration: ring-closing addition of B-O σ bonds across alkynes.

10. 1,2-N-migration in a gold-catalysed synthesis of functionalised indenes by the 1,1-carboalkoxylation of ynamides.