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Literature DB >> 30426753

Intramolecular Vinylation of Aryl Rings by Vinyl Cations.

Abstract

A Lewis acid mediated intramolecular electrophilic vinylation of aryl rings by vinyl cations is reported. This reaction takes advantage of β-hydroxy-α-diazo ketones as vinyl cation precursors and provides good yields of tricyclic 1-indenones that contain a seven-membered ring. Extending the alkane chain that tethers the vinyl cation to the aromatic ring leads to 2-napthol and 2-indenone products.

Entities: Chemical

Year: 2018 PMID： 30426753 PMCID： PMC7045802 DOI： 10.1021/acs.orglett.8b03054

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

12 in total

1. Optimization of the indenone ring of indenoisoquinoline topoisomerase I inhibitors.

Authors: Andrew Morrell; Michael Placzek; Seth Parmley; Brian Grella; Smitha Antony; Yves Pommier; Mark Cushman
Journal: J Med Chem Date: 2007-08-04 Impact factor: 7.446

2. Copper-catalyzed intramolecular aryl-bicyclization of diynes with diaryliodonium salts via vinyl cations.

Authors: Guohua Wang; Chao Chen; Jing Peng
Journal: Chem Commun (Camb) Date: 2016-08-11 Impact factor: 6.222

3. Indenone derivatives: a novel template for peroxisome proliferator-activated receptor gamma (PPARgamma) agonists.

Authors: Jin Hee Ahn; Mi Sik Shin; Sun Ho Jung; Seung Kyu Kang; Kwang Rok Kim; Sang Dal Rhee; Won Hoon Jung; Sung Don Yang; Seung Jun Kim; Joo Rang Woo; Jeong Hyung Lee; Hyae Gyeong Cheon; Sung Soo Kim
Journal: J Med Chem Date: 2006-07-27 Impact factor: 7.446

4. A facile access to 4-substituted-2-naphthols via a tandem Friedel-Crafts reaction: a β-chlorovinyl ketone pathway.

Authors: Hun Young Kim; Kyungsoo Oh
Journal: Org Lett Date: 2014-10-30 Impact factor: 6.005

5. Brønsted acid-promoted cyclizations of siloxyalkynes with arenes and alkenes.

Authors: Liming Zhang; Sergey A Kozmin
Journal: J Am Chem Soc Date: 2004-08-25 Impact factor: 15.419

6. 2-Arylindenes and 2-arylindenones: molecular structures and considerations in the binding orientation of unsymmetrical nonsteroidal ligands to the estrogen receptor.

Authors: G M Anstead; S R Wilson; J A Katzenellenbogen
Journal: J Med Chem Date: 1989-09 Impact factor: 7.446

Intramolecular Vinylation of Aryl Rings by Vinyl Cations.

1. Optimization of the indenone ring of indenoisoquinoline topoisomerase I inhibitors.

2. Copper-catalyzed intramolecular aryl-bicyclization of diynes with diaryliodonium salts via vinyl cations.

3. Indenone derivatives: a novel template for peroxisome proliferator-activated receptor gamma (PPARgamma) agonists.

4. A facile access to 4-substituted-2-naphthols via a tandem Friedel-Crafts reaction: a β-chlorovinyl ketone pathway.

5. Brønsted acid-promoted cyclizations of siloxyalkynes with arenes and alkenes.

6. 2-Arylindenes and 2-arylindenones: molecular structures and considerations in the binding orientation of unsymmetrical nonsteroidal ligands to the estrogen receptor.

7. Formal homologous aldol reactions: interrupting the Nazarov cyclization via carboalkoxylation of alkynes.

8. Teaching an old carbocation new tricks: Intermolecular C-H insertion reactions of vinyl cations.

Review 9. Synthesis of 1-indanones with a broad range of biological activity.

10. Remote C-H insertion of vinyl cations leading to cyclopentenones.

1. Substituted α-Alkylidene Cyclopentenones via the Intramolecular Reaction of Vinyl Cations with Alkenes.

2. Migratory Aptitudes in Rearrangements of Destabilized Vinyl Cations.