Literature DB >> 22070096

Intercepting Wacker intermediates with arenes: C-H functionalization and dearomatization.

Bryan S Matsuura1, Allison G Condie, Ian A McBee, Ryan C Buff, Gregory J Karahalis, Corey R J Stephenson.   

Abstract

An intramolecular cyclization cascade reaction has been developed utilizing a high valent palladium intermediate that generates a carbon-carbon and carbon-oxygen bond in a single transformation. This method provides rapid access to highly functionalized tricyclic scaffolds, including spirocyclic cyclohexadienones. Good yields and mild conditions are reported with high tolerance toward oxygen and water.

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Year:  2011        PMID： 22070096      PMCID： PMC3235802          DOI： 10.1021/ol202881q

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


  46 in total

1.  An intermolecular palladium-catalyzed diamination of unactivated alkenes.

Authors:  Alvaro Iglesias; Edwin G Pérez; Kilian Muñiz
Journal:  Angew Chem Int Ed Engl       Date:  2010-10-25       Impact factor: 15.336

2.  Use of aryl chlorides as electrophiles in Pd-catalyzed alkene difunctionalization reactions.

Authors:  Brandon R Rosen; Joshua E Ney; John P Wolfe
Journal:  J Org Chem       Date:  2010-04-16       Impact factor: 4.354

3.  Palladium-mediated fluorination of arylboronic acids.

Authors:  Takeru Furuya; Hanns Martin Kaiser; Tobias Ritter
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

4.  Emergence of palladium(IV) chemistry in synthesis and catalysis.

Authors:  Petr Sehnal; Richard J K Taylor; Ian J S Fairlamb
Journal:  Chem Rev       Date:  2010-02-10       Impact factor: 60.622

5.  Highly regioselective Pd-catalyzed intermolecular aminoacetoxylation of alkenes and evidence for cis-aminopalladation and S(N)2 C-O bond formation.

Authors:  Guosheng Liu; Shannon S Stahl
Journal:  J Am Chem Soc       Date:  2006-06-07       Impact factor: 15.419

6.  Platensimycin is a selective FabF inhibitor with potent antibiotic properties.

Authors:  Jun Wang; Stephen M Soisson; Katherine Young; Wesley Shoop; Srinivas Kodali; Andrew Galgoci; Ronald Painter; Gopalakrishnan Parthasarathy; Yui S Tang; Richard Cummings; Sookhee Ha; Karen Dorso; Mary Motyl; Hiranthi Jayasuriya; John Ondeyka; Kithsiri Herath; Chaowei Zhang; Lorraine Hernandez; John Allocco; Angela Basilio; José R Tormo; Olga Genilloud; Francisca Vicente; Fernando Pelaez; Lawrence Colwell; Sang Ho Lee; Bruce Michael; Thomas Felcetto; Charles Gill; Lynn L Silver; Jeffery D Hermes; Ken Bartizal; John Barrett; Dennis Schmatz; Joseph W Becker; Doris Cully; Sheo B Singh
Journal:  Nature       Date:  2006-05-18       Impact factor: 49.962

7.  Palladium-catalyzed ring-forming aminoacetoxylation of alkenes.

Authors:  Erik J Alexanian; Chulbom Lee; Erik J Sorensen
Journal:  J Am Chem Soc       Date:  2005-06-01       Impact factor: 15.419

8.  High-oxidation-state palladium catalysis: new reactivity for organic synthesis.

Authors:  Kilian Muñiz
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

9.  Mechanism of N-fluorobenzenesulfonimide promoted diamination and carboamination reactions: divergent reactivity of a Pd(IV) species.

Authors:  Paul A Sibbald; Carolyn F Rosewall; Rodney D Swartz; Forrest E Michael
Journal:  J Am Chem Soc       Date:  2009-11-04       Impact factor: 15.419

10.  Palladium-catalyzed carboamination of alkenes promoted by N-fluorobenzenesulfonimide via C-H activation of arenes.

Authors:  Carolyn F Rosewall; Paul A Sibbald; Dmitry V Liskin; Forrest E Michael
Journal:  J Am Chem Soc       Date:  2009-07-15       Impact factor: 15.419
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  9 in total

1.  Copper-catalyzed intramolecular alkene carboetherification: synthesis of fused-ring and bridged-ring tetrahydrofurans.

Authors:  Yan Miller; Lei Miao; Azade S Hosseini; Sherry R Chemler
Journal:  J Am Chem Soc       Date:  2012-07-05       Impact factor: 15.419

2.  Copper-catalyzed oxytrifluoromethylation of unactivated alkenes.

Authors:  Rong Zhu; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2012-07-23       Impact factor: 15.419

3.  Combined oxypalladation/C-H functionalization: palladium(II)-catalyzed intramolecular oxidative oxyarylation of hydroxyalkenes.

Authors:  Rong Zhu; Stephen L Buchwald
Journal:  Angew Chem Int Ed Engl       Date:  2012-01-11       Impact factor: 15.336

4.  Palladium(II)-Catalyzed Tandem Oxidative Acetoxylation/ortho C-H Activation/Carbocyclization of Arylallenes.

Authors:  Javier Mazuela; Debasis Banerjee; Jan-E Bäckvall
Journal:  J Am Chem Soc       Date:  2015-07-28       Impact factor: 15.419

5.  Versatile Enantioselective Synthesis of Functionalized Lactones via Copper-Catalyzed Radical Oxyfunctionalization of Alkenes.

Authors:  Rong Zhu; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2015-06-23       Impact factor: 15.419

6.  Highly Efficient Cascade Reaction for Selective Formation of Spirocyclobutenes from Dienallenes via Palladium-Catalyzed Oxidative Double Carbocyclization-Carbonylation-Alkynylation.

Authors:  Youai Qiu; Bin Yang; Can Zhu; Jan-E Bäckvall
Journal:  J Am Chem Soc       Date:  2016-10-13       Impact factor: 15.419

7.  Palladium-catalyzed oxidative acyloxylation/carbocyclization of allenynes.

Authors:  Youqian Deng; Jan-E Bäckvall
Journal:  Angew Chem Int Ed Engl       Date:  2013-02-05       Impact factor: 15.336

8.  Control of selectivity in palladium-catalyzed oxidative carbocyclization/borylation of allenynes.

Authors:  Youqian Deng; Teresa Bartholomeyzik; Jan-E Bäckvall
Journal:  Angew Chem Int Ed Engl       Date:  2013-05-17       Impact factor: 15.336

9.  Fe-catalyzed Decarbonylative Alkylative Spirocyclization of N-Arylcinnamamides: Access to Alkylated 1-Azaspirocyclohexadienones.

Authors:  Xiang Peng; Ren-Xiang Liu; Xiang-Yan Xiao; Luo Yang
Journal:  Molecules       Date:  2020-01-21       Impact factor: 4.411
  9 in total

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