Synthesis of 2-Naphthols via Carbonylative Stille Coupling Reaction of 2-Bromobenzyl Bromides with Tributylallylstannane Followed by the Heck Reaction
Release Time:2019-03-09 Hits:
Indexed by: Journal Article
Date of Publication: 2011-12-16
Journal: JOURNAL OF ORGANIC CHEMISTRY
Included Journals: PubMed、SCIE、Scopus
Volume: 76
Issue: 24
Page Number: 10068-10077
ISSN: 0022-3263
Abstract: A method for the synthesis of 2-naphthols 4 is described. The carbonylative Stifle coupling reactions of 2-bromobenzyl bromides with tributylallylstannane to produce 2-bromobenzyl beta,gamma-unsaturated ketones 2 in satisfactory to excellent yields has been achieved. The isomerization of 2-bromobenzyl beta,gamma-unsaturated ketones 2 can readily occur under basic conditions to generate 2-bromobenzyl alpha,beta-unsaturated ketones 3. The 2-bromobenzyl alpha,beta-unsaturated ketones 3 can be transformed into 2-naphthols 4 via intramolecular Heck reaction in satisfactory to good yields.
Prev One:Preparation and application of air-stable P,N-bidentate ligands for the selective synthesis of delta-lactone via the palladium-catalyzed telomerization of 1,3-butadiene with carbon dioxide
Next One:Nucleophilic Dearomatization of Chloromethyl Naphthalene Derivatives via eta(3)-Benzylpalladium Intermediates: A New Strategy for Catalytic Dearomatization