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Literature DB >> 28392926

Synthesis of 2,3-Dihydrobenzofurans via the Palladium Catalyzed Carboalkoxylation of 2-Allylphenols.

Abstract

A new Pd-catalyzed alkene carboalkoxylation strategy for the preparation of 2,3-dihydrobenzofurans is described. This method effects the coupling of readily available 2-allylphenol derivatives with aryl triflates to generate a wide range of functionalized 2,3-dihydrobenzofurans in good yields and diastereoselectivities (up to >20:1). Use of newly developed reaction conditions that promote anti-heteropalladation of the alkene is essential in order to generate products in high yield.

Entities: Chemical Gene

Year: 2016 PMID： 28392926 PMCID： PMC5382964 DOI： 10.1039/C6QO00215C

Source DB: PubMed Journal: Org Chem Front ISSN： 2052-4110 Impact factor: 5.281

31 in total

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Authors: Shu Yuan Li; Hiroyuki Fuchino; Nobuo Kawahara; Setsuko Sekita; Motoyoshi Satake
Journal: J Nat Prod Date: 2002-03 Impact factor: 4.050

2. Chartarlactams A-P, phenylspirodrimanes from the sponge-associated fungus Stachybotrys chartarum with antihyperlipidemic activities.

Authors: Yong Li; Chongming Wu; Dong Liu; Peter Proksch; Peng Guo; Wenhan Lin
Journal: J Nat Prod Date: 2014-01-03 Impact factor: 4.050

3. Palladium-Catalyzed Alkene Carboamination Reactions of Electron-Poor Nitrogen Nucleophiles.

Authors: Luke J Peterson; John P Wolfe
Journal: Adv Synth Catal Date: 2015-07-14 Impact factor: 5.837

4. Palladium-catalyzed synthesis of N-aryl-2-benzylindolines via tandem arylation of 2-allylaniline: control of selectivity through in situ catalyst modification.

Authors: Ricardo Lira; John P Wolfe
Journal: J Am Chem Soc Date: 2004-11-03 Impact factor: 15.419

5. Influence of catalyst structure and reaction conditions on anti- versus syn-aminopalladation pathways in Pd-catalyzed alkene carboamination reactions of N-allylsulfamides.

Authors: Ryan M Fornwald; Jonathan A Fritz; John P Wolfe
Journal: Chemistry Date: 2014-06-17 Impact factor: 5.236

6. Mechanistic studies of Wacker-type amidocyclization of alkenes catalyzed by (IMes)Pd(TFA)2(H2O): kinetic and stereochemical implications of proton transfer.

Authors: Xuan Ye; Paul B White; Shannon S Stahl
Journal: J Org Chem Date: 2012-11-30 Impact factor: 4.354

7. Synthetic analogue of rocaglaol displays a potent and selective cytotoxicity in cancer cells: involvement of apoptosis inducing factor and caspase-12.

Authors: Frédéric Thuaud; Yohann Bernard; Gülen Türkeri; Ronan Dirr; Geneviève Aubert; Thierry Cresteil; Aurélie Baguet; Catherine Tomasetto; Yuri Svitkin; Nahum Sonenberg; Canan G Nebigil; Laurent Désaubry
Journal: J Med Chem Date: 2009-08-27 Impact factor: 7.446

Synthesis of 2,3-Dihydrobenzofurans via the Palladium Catalyzed Carboalkoxylation of 2-Allylphenols.

1. New phenolic constituents from Smilax bracteata.

2. Chartarlactams A-P, phenylspirodrimanes from the sponge-associated fungus Stachybotrys chartarum with antihyperlipidemic activities.

3. Palladium-Catalyzed Alkene Carboamination Reactions of Electron-Poor Nitrogen Nucleophiles.

4. Palladium-catalyzed synthesis of N-aryl-2-benzylindolines via tandem arylation of 2-allylaniline: control of selectivity through in situ catalyst modification.

5. Influence of catalyst structure and reaction conditions on anti- versus syn-aminopalladation pathways in Pd-catalyzed alkene carboamination reactions of N-allylsulfamides.

6. Mechanistic studies of Wacker-type amidocyclization of alkenes catalyzed by (IMes)Pd(TFA)2(H2O): kinetic and stereochemical implications of proton transfer.

7. Synthetic analogue of rocaglaol displays a potent and selective cytotoxicity in cancer cells: involvement of apoptosis inducing factor and caspase-12.

8. Diarylation of alkenes by a Cu-catalyzed migratory insertion/cross-coupling cascade.

9. The syn/anti-dichotomy in the palladium-catalyzed addition of nucleophiles to alkenes.

10. Catalytic enantioselective cyclization/cross-coupling with alkyl electrophiles.

1. Recent Developments in Pd(0)-Catalyzed Alkene Carboheterofunctionalization Reactions.

Review 2. Recent Advances in Phthalan and Coumaran Chemistry.

3. Pd/Xiang-Phos-catalyzed enantioselective intermolecular carboheterofunctionalization under mild conditions.