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Literature DB >> 17249786

Mild conditions for the synthesis of functionalized pyrrolidines via Pd-catalyzed carboamination reactions.

Myra Beaudoin Bertrand¹, Matthew L Leathen, John P Wolfe.

Abstract

[reaction: see text] The palladium-catalyzed carboamination of N-protected gamma-aminoalkenes with aryl bromides and triflates has been achieved under new, mild reaction conditions using the weak base Cs(2)CO(3) in dioxane solvent. These reactions tolerate a wide variety of functional groups, including enolizable ketones, nitro groups, methyl esters, and acetates, which are not compatible with previously described conditions.

Entities: Chemical

Mesh：

Substances：

Year: 2007 PMID： 17249786 PMCID： PMC2758105 DOI： 10.1021/ol062808f

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

12 in total

1. Intramolecular dipolar cycloaddition reactions of azomethine ylides.

Authors: Iain Coldham; Richard Hufton
Journal: Chem Rev Date: 2005-07 Impact factor: 60.622

2. Synthesis of pyrrolidines via palladium(II)-catalyzed aerobic oxidative carboamination of butyl vinyl ether and styrenes with allyl tosylamides.

Authors: Christopher C Scarborough; Shannon S Stahl
Journal: Org Lett Date: 2006-07-20 Impact factor: 6.005

3. Palladium-catalyzed tandem N-arylation/carboamination reactions for the stereoselective synthesis of N-aryl-2-benzyl pyrrolidines.

Authors: Qifei Yang; Joshua E Ney; John P Wolfe
Journal: Org Lett Date: 2005-06-23 Impact factor: 6.005

4. 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

5. Synthesis of N-Aryl-2-allyl Pyrrolidines via Palladium-catalyzed Carboamination Reactions of γ-(N-Arylamino)alkenes with Vinyl Bromides.

Authors: Joshua E Ney; Michael B Hay; Qifei Yang; John P Wolfe
Journal: Adv Synth Catal Date: 2005-10-01 Impact factor: 5.837

6. 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

7. Palladium(II)-Catalyzed Intramolecular Aminocarbonylation of endo-Carbamates under Wacker-Type Conditions.

Authors: Hiroto Harayama; Atsuhiro Abe; Tomonori Sakado; Masanari Kimura; Keigo Fugami; Shuji Tanaka; Yoshinao Tamaru
Journal: J Org Chem Date: 1997-04-04 Impact factor: 4.354

8. 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

9. Reevaluation of the mechanism of the amination of aryl halides catalyzed by BINAP-ligated palladium complexes.

Authors: Shashank Shekhar; Per Ryberg; John F Hartwig; Jinu S Mathew; Donna G Blackmond; Eric R Strieter; Stephen L Buchwald
Journal: J Am Chem Soc Date: 2006-03-22 Impact factor: 15.419

10. Copper(II) acetate promoted oxidative cyclization of arylsulfonyl-o-allylanilines.

Authors: Eric S Sherman; Sherry R Chemler; Tai Boon Tan; Oksana Gerlits
Journal: Org Lett Date: 2004-05-13 Impact factor: 6.005

14 in total

1. 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

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

Authors: Zachary J Garlets; Derick R White; John P Wolfe
Journal: Asian J Org Chem Date: 2017-03-10 Impact factor: 3.319

3. Gold-catalyzed intramolecular aminoarylation of alkenes: C-C bond formation through bimolecular reductive elimination.

Authors: William E Brenzovich; Diego Benitez; Aaron D Lackner; Hunter P Shunatona; Ekaterina Tkatchouk; William A Goddard; F Dean Toste
Journal: Angew Chem Int Ed Engl Date: 2010-07-26 Impact factor: 15.336

4. Influence of hydroxylamine conformation on stereocontrol in Pd-catalyzed isoxazolidine-forming reactions.

Authors: Georgia S Lemen; Natalie C Giampietro; Michael B Hay; John P Wolfe
Journal: J Org Chem Date: 2009-03-20 Impact factor: 4.354

5. Stereoselective Synthesis of Saturated Heterocycles via Pd-Catalyzed Alkene Carboetherification and Carboamination Reactions.

Authors: John P Wolfe
Journal: Synlett Date: 2006-11-13 Impact factor: 2.454

6. A concise asymmetric synthesis of cis-2,6-disubstituted N-aryl piperazines via Pd-catalyzed carboamination reactions.

Authors: Josephine S Nakhla; John P Wolfe
Journal: Org Lett Date: 2007-07-25 Impact factor: 6.005

7. 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

8. Stereoselective synthesis of imidazolidin-2-ones via Pd-catalyzed alkene carboamination. Scope and limitations.

Authors: Jonathan A Fritz; John P Wolfe
Journal: Tetrahedron Date: 2008 Impact factor: 2.457

9. Palladium-catalyzed synthesis of cyclopentane-fused benzocyclobutenes via tandem directed carbopalladation/C-H bond functionalization.

Authors: Myra Beaudoin Bertrand; John P Wolfe
Journal: Org Lett Date: 2007-07-07 Impact factor: 6.005

10. Copper(II) carboxylate-promoted intramolecular carboamination of alkenes for the synthesis of polycyclic lactams.

Authors: Peter H Fuller; Sherry R Chemler
Journal: Org Lett Date: 2007-11-29 Impact factor: 6.005