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Literature DB >> 24313353

Straightforward assembly of benzoxepines by means of a rhodium(III)-catalyzed C-H functionalization of o-vinylphenols.

Andrés Seoane¹, Noelia Casanova, Noelia Quiñones, José L Mascareñas, Moisés Gulías.

Abstract

Readily available o-vinylphenols undergo a formal (5 + 2) cycloaddition to alkynes when treated with catalytic amounts of [Cp*RhCl2]2 and Cu(OAc)2. The reaction, which involves the cleavage of the terminal C-H bond of the alkenyl moiety, generates highly valuable benzoxepine skeletons in a practical, versatile, and atom-economical manner. Using carbon monoxide instead of an alkyne as reaction partner leads to coumarin products which formally result from a (5 + 1) cycloaddition.

Entities: Chemical

Year: 2013 PMID： 24313353 DOI： 10.1021/ja410538w

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

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Cited

9 in total

1. Reversed reactivity of anilines with alkynes in the rhodium-catalysed C-H activation/carbonylation tandem.

Authors: Siba P Midya; Manoj K Sahoo; Vinod G Landge; P R Rajamohanan; Ekambaram Balaraman
Journal: Nat Commun Date: 2015-10-21 Impact factor: 14.919

2. Palladium(II)-Catalyzed Annulation between ortho-Alkenylphenols and Allenes. Key Role of the Metal Geometry in Determining the Reaction Outcome.

Authors: Noelia Casanova; Karina P Del Rio; Rebeca García-Fandiño; José L Mascareñas; Moisés Gulías
Journal: ACS Catal Date: 2016-04-14 Impact factor: 13.084

3. Palladium-Catalyzed, Enantioselective Formal Cycloaddition between Benzyltriflamides and Allenes: Straightforward Access to Enantioenriched Isoquinolines.

Authors: Xandro Vidal; José L Mascareñas; Moisés Gulías
Journal: J Am Chem Soc Date: 2019-01-22 Impact factor: 15.419

4. All-Carbon [3+3] Oxidative Annulations of 1,3-Enynes by Rhodium(III)-Catalyzed C-H Functionalization and 1,4-Migration.

Authors: David J Burns; Daniel Best; Martin D Wieczysty; Hon Wai Lam
Journal: Angew Chem Int Ed Engl Date: 2015-07-15 Impact factor: 15.336

Straightforward assembly of benzoxepines by means of a rhodium(III)-catalyzed C-H functionalization of o-vinylphenols.

1. Reversed reactivity of anilines with alkynes in the rhodium-catalysed C-H activation/carbonylation tandem.

2. Palladium(II)-Catalyzed Annulation between ortho-Alkenylphenols and Allenes. Key Role of the Metal Geometry in Determining the Reaction Outcome.

3. Palladium-Catalyzed, Enantioselective Formal Cycloaddition between Benzyltriflamides and Allenes: Straightforward Access to Enantioenriched Isoquinolines.

4. All-Carbon [3+3] Oxidative Annulations of 1,3-Enynes by Rhodium(III)-Catalyzed C-H Functionalization and 1,4-Migration.

5. Rhodium(III)-catalyzed dearomatizing (3 + 2) annulation of 2-alkenylphenols and alkynes.

6. Origins of unique gold-catalysed chemo- and site-selective C-H functionalization of phenols with diazo compounds.

7. Rh^I/Rh^III catalyst-controlled divergent aryl/heteroaryl C-H bond functionalization of picolinamides with alkynes.

8. Rhodium(III)-Catalyzed Intramolecular Annulations of Acrylic and Benzoic Acids to Alkynes.

9. Aryl derivatives of 3H-1,2-benzoxathiepine 2,2-dioxide as carbonic anhydrase inhibitors.