Literature DB >> 20297834

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

Brandon R Rosen1, Joshua E Ney, John P Wolfe.   

Abstract

The development of conditions that allow use of inexpensive aryl chlorides as electrophiles in Pd-catalyzed alkene carboamination and carboetherification reactions is described. A catalyst composed of Pd(OAc)(2) and S-Phos minimizes N-arylation of the substrate and prevents formation of mixtures of regioisomeric products. A number of heterocycles, including pyrrolidines, isoxazolidines, tetrahydrofurans, and pyrazolidines, are efficiently generated with this method.

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Year:  2010        PMID： 20297834      PMCID： PMC2853027          DOI： 10.1021/jo100344k

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  29 in total

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2.  Palladium-catalyzed alkene carboamination reactions for the synthesis of substituted piperazines.

Authors:  Josephine S Nakhla; Danielle M Schultz; John P Wolfe
Journal:  Tetrahedron       Date:  2009-09-15       Impact factor: 2.457

3.  Copper(II)-catalyzed enantioselective intramolecular carboamination of alkenes.

Authors:  Wei Zeng; Sherry R Chemler
Journal:  J Am Chem Soc       Date:  2007-10-05       Impact factor: 15.419

4.  Synthesis of aziridines by palladium-catalyzed reactions of allylamines with aryl and alkenyl halides: evidence of a syn-carboamination pathway.

Authors:  Sayuri Hayashi; Hideki Yorimitsu; Koichiro Oshima
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

5.  Selective synthesis of 5- or 6-aryl octahydrocyclopenta[b]pyrroles from a common precursor through control of competing pathways in a Pd-catalyzed reaction.

Authors:  Joshua E Ney; John P Wolfe
Journal:  J Am Chem Soc       Date:  2005-06-22       Impact factor: 15.419

6.  Palladium-catalyzed synthesis of N-aryl pyrrolidines from gamma-(N-Arylamino) alkenes: evidence for chemoselective alkene insertion into Pd--N bonds.

Authors:  Joshua E Ney; John P Wolfe
Journal:  Angew Chem Int Ed Engl       Date:  2004-07-05       Impact factor: 15.336

7.  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

8.  Mild conditions for Pd-catalyzed carboamination of N-protected hex-4-enylamines and 1-, 3-, and 4-substituted pent-4-enylamines. Scope, limitations, and mechanism of pyrrolidine formation.

Authors:  Myra Beaudoin Bertrand; Joshua D Neukom; John P Wolfe
Journal:  J Org Chem       Date:  2008-10-23       Impact factor: 4.354

9.  Palladium-catalyzed highly stereoselective synthesis of N-aryl-3-arylmethylisoxazolidines via tandem arylation of O-homoallylhydroxylamines.

Authors:  Jinsong Peng; Wenqing Lin; Shixue Yuan; Yuanwei Chen
Journal:  J Org Chem       Date:  2007-03-17       Impact factor: 4.354

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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  7 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.  Intramolecular alkene carboamination reactions for the synthesis of enantiomerically enriched tropane derivatives.

Authors:  Danielle M Schultz; John P Wolfe
Journal:  Org Lett       Date:  2011-05-11       Impact factor: 6.005

3.  Cascade intramolecular N-arylation/intermolecular carboamination reactions for the construction of tricyclic heterocycles.

Authors:  Georgia S Lemen; John P Wolfe
Journal:  Org Lett       Date:  2011-05-23       Impact factor: 6.005

4.  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

5.  Recent Developments in Pd-Catalyzed Alkene Aminoarylation Reactions for the Synthesis of Nitrogen Heterocycles.

Authors:  Danielle M Schultz; John P Wolfe
Journal:  Synthesis (Stuttg)       Date:  2012       Impact factor: 3.157

6.  Allylation of isatin-derived N-Boc-hydrazones followed by Pd-catalyzed carboamination reaction: an entry to 3-spiro-pyrazolidyl-oxindoles.

Authors:  Stefano Gazzotti; Marco Manenti; Leonardo Lo Presti; Alessandra Silvani
Journal:  RSC Adv       Date:  2019-11-20       Impact factor: 4.036

7.  Catalyst-free carbosilylation of alkenes using silyl boronates and organic fluorides via selective C-F bond activation.

Authors:  Jun Zhou; Bingyao Jiang; Yamato Fujihira; Zhengyu Zhao; Takanori Imai; Norio Shibata
Journal:  Nat Commun       Date:  2021-06-18       Impact factor: 14.919
  7 in total

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