Literature DB >> 20000487

Pd-catalyzed intramolecular oxyalkynylation of alkenes with hypervalent iodine.

Stefano Nicolai1, Stéphane Erard, Davinia Fernández González, Jérôme Waser.   

Abstract

The first example of intramolecular oxyalkynylation of nonactivated alkenes using oxidative Pd chemistry is reported. Both phenol and aromatic or aliphatic acid derivatives could be used under operator-friendly conditions (room temperature, technical solvents, under air). The discovery of the superiority of benziodoxolone-derived hypervalent iodine reagent 3d as an alkyne transfer reagent further expands the rapidly increasing utility of hypervalent iodine reagents in catalysis and is expected to have important implications for other similar processes.

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Year:  2010        PMID: 20000487     DOI: 10.1021/ol9027286

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


  12 in total

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

Authors:  Bryan S Matsuura; Allison G Condie; Ian A McBee; Ryan C Buff; Gregory J Karahalis; Corey R J Stephenson
Journal:  Org Lett       Date:  2011-11-09       Impact factor: 6.005

2.  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

3.  Highly diastereoselective Pd-catalyzed carboetherification reactions of acyclic internal alkenes. Stereoselective synthesis of polysubstituted tetrahydrofurans.

Authors:  Amanda F Ward; John P Wolfe
Journal:  Org Lett       Date:  2010-03-19       Impact factor: 6.005

4.  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

5.  Synthesis of chromans via Pd-catalyzed alkene carboetherification reactions.

Authors:  Amanda F Ward; Yan Xu; John P Wolfe
Journal:  Chem Commun (Camb)       Date:  2011-11-24       Impact factor: 6.222

6.  Enantioselective copper-catalyzed carboetherification of unactivated alkenes.

Authors:  Michael T Bovino; Timothy W Liwosz; Nicole E Kendel; Yan Miller; Nina Tyminska; Eva Zurek; Sherry R Chemler
Journal:  Angew Chem Int Ed Engl       Date:  2014-05-05       Impact factor: 15.336

7.  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

8.  Synthesis of Phthalans Via Copper-Catalyzed Enantioselective Cyclization/Carboetherification of 2-Vinylbenzyl Alcohols.

Authors:  Dake Chen; Sherry R Chemler
Journal:  Org Lett       Date:  2018-10-11       Impact factor: 6.005

9.  One-pot gold-catalyzed synthesis of 3-silylethynyl indoles from unprotected o-alkynylanilines.

Authors:  Jonathan P Brand; Clara Chevalley; Jérôme Waser
Journal:  Beilstein J Org Chem       Date:  2011-05-04       Impact factor: 2.883

10.  One-pot, three-component arylalkynyl sulfone synthesis.

Authors:  C Chun Chen; Jerome Waser
Journal:  Org Lett       Date:  2015-01-29       Impact factor: 6.005

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