Literature DB >> 32309953

Palladium-Catalyzed Disilylation and Digermanylation of Alkene Tethered Aryl Halides: Direct Access to Versatile Silylated and Germanylated Heterocycles.

Marco Wollenburg1,2, Jonathan Bajohr2, Austin D Marchese2, Andrew Whyte2, Frank Glorius1, Mark Lautens2.   

Abstract

A method for the palladium-catalyzed disilylation and digermanylation of aryl halides bearing a tethered alkene has been developed. The mechanism is thought to proceed via Heck-type cyclization, followed by C-H activation, resulting in a reactive fused-palladacycle. A wide variety of disilylated and digermanylated heterocycles are obtained from readily available aryl halides in high yields with various functional groups. Moreover, the developed protocol proved to be highly diastereoselective.

Entities:  

Year:  2020        PMID: 32309953     DOI: 10.1021/acs.orglett.0c01169

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


  3 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.  Mapping Ambiphile Reactivity Trends in the Anti-(Hetero)annulation of Non-Conjugated Alkenes via PdII /PdIV Catalysis.

Authors:  Hui-Qi Ni; Phillippa Cooper; Shouliang Yang; Fen Wang; Neal Sach; Pranali G Bedekar; Joyann S Donaldson; Michelle Tran-Dubé; Indrawan J McAlpine; Keary M Engle
Journal:  Angew Chem Int Ed Engl       Date:  2022-02-02       Impact factor: 15.336

3.  Selective radical cascade (4+2) annulation with olefins towards the synthesis of chroman derivatives via organo-photoredox catalysis.

Authors:  Zhipeng Guan; Xingxing Zhong; Yayu Ye; Xiangwei Li; Hengjiang Cong; Hong Yi; Heng Zhang; Zhiliang Huang; Aiwen Lei
Journal:  Chem Sci       Date:  2022-04-21       Impact factor: 9.969

  3 in total

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