Literature DB >> 15496105

Water enables direct use of allyl alcohol for Tsuji-Trost reaction without activators.

Hidenori Kinoshita1, Hiroshi Shinokubo, Koichiro Oshima.   

Abstract

[reaction: see text] An aqueous biphasic reaction system enables the direct use of allyl alcohol in the Tsuji-Trost reaction without the help of any activating reagents for allyl alcohol. The reaction conditions are neutral to basic, allowing the use of amines as the nucleophile. Theoretical calculations have elucidated the importance of hydration of the hydroxy group for the smooth generation of pi-allylpalladium species.

Entities:  

Year:  2004        PMID： 15496105     DOI： 10.1021/ol048207a

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


  14 in total

1.  Deacylative allylation: allylic alkylation via retro-Claisen activation.

Authors:  Alexander J Grenning; Jon A Tunge
Journal:  J Am Chem Soc       Date:  2011-08-24       Impact factor: 15.419

2.  Enantioselective Intramolecular Allylic Substitution via Synergistic Palladium/Chiral Phosphoric Acid Catalysis: Insight into Stereoinduction through Statistical Modeling.

Authors:  Cheng-Che Tsai; Christopher Sandford; Tao Wu; Buyun Chen; Matthew S Sigman; F Dean Toste
Journal:  Angew Chem Int Ed Engl       Date:  2020-06-30       Impact factor: 15.336

3.  Gold(I)-catalyzed amination of allylic alcohols with cyclic ureas and related nucleophiles.

Authors:  Paramita Mukherjee; Ross A Widenhoefer
Journal:  Org Lett       Date:  2010-03-19       Impact factor: 6.005

4.  Gold(I)-catalyzed intramolecular amination of allylic alcohols with alkylamines.

Authors:  Paramita Mukherjee; Ross A Widenhoefer
Journal:  Org Lett       Date:  2011-02-11       Impact factor: 6.005

5.  Deacylative allylation of nitroalkanes: unsymmetric bisallylation by a three-component coupling.

Authors:  Alexander J Grenning; Jon A Tunge
Journal:  Angew Chem Int Ed Engl       Date:  2010-12-29       Impact factor: 15.336

6.  A computational approach to the synthesis of 1,3,5-thiadiazinane-2-thiones in aqueous medium: theoretical evidence for water-promoted heterocyclization.

Authors:  Julieta Coro; Ramon Alvarez-Puebla; Ana L Montero; Margarita Suárez; Nazario Martin; Rolando Perez-Pineiro
Journal:  J Mol Model       Date:  2008-05-17       Impact factor: 1.810

7.  Et3B-mediated and palladium-catalyzed direct allylation of β-dicarbonyl compounds with Morita-Baylis-Hillman alcohols.

Authors:  Ahlem Abidi; Yosra Oueslati; Farhat Rezgui
Journal:  Beilstein J Org Chem       Date:  2016-11-15       Impact factor: 2.883

8.  Tsuji-Trost Cyclization of Disulfonamides: Synthesis of 12-Membered, 11-Membered, and Pyridine-Fused Macrocyclic Triamines.

Authors:  Rameez Ali; Sreenivasa Anugu; Reena Chawla; Violeta G Demillo; Florian Goulinet-Mateo; Sagar Gyawali; Sunil Hamal; Dylan E Jones; Katrin Lamprecht; Truc Le; Liezel A Lumangtad; Nicholas C Pflug; Alekhya Sama; Emily D Scarbrough; Thomas W Bell
Journal:  ACS Omega       Date:  2019-01-15

9.  Activation of alcohols with carbon dioxide: intermolecular allylation of weakly acidic pronucleophiles.

Authors:  Simon B Lang; Theresa M Locascio; Jon A Tunge
Journal:  Org Lett       Date:  2014-08-04       Impact factor: 6.005

10.  Exploring the Mechanism of the Palladium-Catalyzed 3-Butene-2-ol Amination Reaction: A DFT Study.

Authors:  Lingshan Lyu; Wei Feng; Siwei Yang; Huiling Liu; Xuri Huang
Journal:  Front Chem       Date:  2020-02-21       Impact factor: 5.221
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