Literature DB >> 21162529

Palladium-catalyzed allylic C-OH functionalization for efficient synthesis of functionalized allylsilanes.

Nicklas Selander1, Jennifer R Paasch, Kálmán J Szabó.   

Abstract

A new method is described for palladium-catalyzed allylic silylation using allylic alcohols and disilanes as precursors. The reactions proceed smoothly under mild and neutral conditions, and this method is suitable for synthesis of regio- and stereodefined allylsilanes. The presented silylation reaction can be easily extended to include synthesis of allylboronates by change of the dimetallic reagent. The presented synthetic procedure offers a broad platform for the selective synthesis of functionalized allyl metal reagents, which are useful precursors in advanced organic chemistry and natural product synthesis.

Entities:  

Year:  2010        PMID: 21162529     DOI: 10.1021/ja1096732

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  7 in total

1.  An Electroreductive Approach to Radical Silylation via the Activation of Strong Si-Cl Bond.

Authors:  Lingxiang Lu; Juno C Siu; Yihuan Lai; Song Lin
Journal:  J Am Chem Soc       Date:  2020-12-08       Impact factor: 15.419

2.  Development of asymmetric deacylative allylation.

Authors:  Alexander J Grenning; Christie K Van Allen; Tapan Maji; Simon B Lang; Jon A Tunge
Journal:  J Org Chem       Date:  2013-07-01       Impact factor: 4.354

3.  Silyl-Heck Reactions for the Preparation of Unsaturated Organosilanes.

Authors:  Sara E S Martin; Donald A Watson
Journal:  Synlett       Date:  2013-09-30       Impact factor: 2.454

4.  Palladium-catalyzed synthesis and isolation of functionalized allylboronic acids: selective, direct allylboration of ketones.

Authors:  Mihai Raducan; Rauful Alam; Kálmán J Szabó
Journal:  Angew Chem Int Ed Engl       Date:  2012-11-19       Impact factor: 15.336

5.  Synthetic Studies of the Rubellin Natural Products: Development of a Stereoselective Strategy and Total Synthesis of (+)-Rubellin C.

Authors:  Jackson A Gartman; Uttam K Tambar
Journal:  J Org Chem       Date:  2021-07-21       Impact factor: 4.198

6.  Cobalt-catalyzed regioselective stereoconvergent Markovnikov 1,2-hydrosilylation of conjugated dienes.

Authors:  Hui Leng Sang; Songjie Yu; Shaozhong Ge
Journal:  Chem Sci       Date:  2017-11-27       Impact factor: 9.825

7.  Transition-Metal-Free Borylation of Allylic and Propargylic Alcohols.

Authors:  Núria Miralles; Rauful Alam; Kálmán J Szabó; Elena Fernández
Journal:  Angew Chem Int Ed Engl       Date:  2016-03-02       Impact factor: 15.336

  7 in total

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