Literature DB >> 23734834

Palladium-catalyzed intermolecular aminoacetoxylation of alkenes and the influence of PhI(OAc)2 on aminopalladation stereoselectivity.

Claudio Martínez1, Yichen Wu, Adam B Weinstein, Shannon S Stahl, Guosheng Liu, Kilian Muñiz.   

Abstract

A modified protocol has been identified for Pd-catalyzed intermolecular aminoacetoxylation of terminal and internal alkenes that enables the alkene to be used as the limiting reagent. The results prompt a reassessment of the stereochemical course of these reactions. X-ray crystallographic characterization of two of the products, together with isotopic labeling studies, show that the amidopalladation step switches from a cis-selective process under aerobic conditions to a trans-selective process in the presence of diacetoxyiodobenzene.

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Year:  2013        PMID： 23734834      PMCID： PMC3703867          DOI： 10.1021/jo400671q

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


  32 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.  Connecting binuclear Pd(III) and mononuclear Pd(IV) chemistry by Pd-Pd bond cleavage.

Authors:  David C Powers; Eunsung Lee; Alireza Ariafard; Melanie S Sanford; Brian F Yates; Allan J Canty; Tobias Ritter
Journal:  J Am Chem Soc       Date:  2012-07-17       Impact factor: 15.419

3.  Studies of reductive elimination reactions to form carbon-oxygen bonds from Pt(IV) complexes.

Authors:  B S Williams; K I Goldberg
Journal:  J Am Chem Soc       Date:  2001-03-21       Impact factor: 15.419

4.  Bimetallic redox synergy in oxidative palladium catalysis.

Authors:  David C Powers; Tobias Ritter
Journal:  Acc Chem Res       Date:  2011-10-27       Impact factor: 22.384

5.  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

Review 6.  High-valent organometallic copper and palladium in catalysis.

Authors:  Amanda J Hickman; Melanie S Sanford
Journal:  Nature       Date:  2012-04-11       Impact factor: 49.962

7.  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

8.  Synthesis of heterocycles via palladium pi-olefin and pi-alkyne chemistry.

Authors:  Gilson Zeni; Richard C Larock
Journal:  Chem Rev       Date:  2004-05       Impact factor: 60.622

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 aerobic oxidative amination of alkenes: development of intra- and intermolecular aza-Wacker reactions.

Authors:  Vasily Kotov; Christopher C Scarborough; Shannon S Stahl
Journal:  Inorg Chem       Date:  2007-03-19       Impact factor: 5.165
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  11 in total

1.  Directed, Palladium(II)-Catalyzed Intermolecular Aminohydroxylation of Alkenes Using a Mild Oxidation System.

Authors:  Tian Zeng; Zhen Liu; Michael A Schmidt; Martin D Eastgate; Keary M Engle
Journal:  Org Lett       Date:  2018-06-11       Impact factor: 6.005

2.  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

3.  Asymmetric Palladium-Catalyzed Alkene Carboamination Reactions for the Synthesis of Cyclic Sulfamides.

Authors:  Zachary J Garlets; Kaia R Parenti; John P Wolfe
Journal:  Chemistry       Date:  2016-03-10       Impact factor: 5.236

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

Authors:  Johnathon T Hutt; John P Wolfe
Journal:  Org Chem Front       Date:  2016-08-22       Impact factor: 5.281

5.  Palladium-Catalyzed Aerobic Intramolecular Aminoacetoxylation of Alkenes Enabled by Catalytic Nitrate.

Authors:  Jiaming Li; Robert H Grubbs; Brian M Stoltz
Journal:  Org Lett       Date:  2016-10-18       Impact factor: 6.005

6.  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

7.  Synthesis of vicinal aminoalcohols by stereoselective aza-Wacker cyclizations: access to (-)-acosamine by redox relay.

Authors:  Adam B Weinstein; David P Schuman; Zhi Xu Tan; Shannon S Stahl
Journal:  Angew Chem Int Ed Engl       Date:  2013-09-17       Impact factor: 15.336

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

Authors:  Pavel Kočovský; Jan-E Bäckvall
Journal:  Chemistry       Date:  2014-11-05       Impact factor: 5.236

9.  Palladium-catalysed anti-Markovnikov selective oxidative amination.

Authors:  Daniel G Kohler; Samuel N Gockel; Jennifer L Kennemur; Peter J Waller; Kami L Hull
Journal:  Nat Chem       Date:  2018-01-01       Impact factor: 24.427

Review 10.  Palladium-Catalyzed Organic Reactions Involving Hypervalent Iodine Reagents.

Authors:  Samata E Shetgaonkar; Ritu Mamgain; Kotaro Kikushima; Toshifumi Dohi; Fateh V Singh
Journal:  Molecules       Date:  2022-06-17       Impact factor: 4.927
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