Literature DB >> 29115722

Radical Cyclization of Alkene-Tethered Ketones Initiated by Hydrogen-Atom Transfer.

Mar Saladrigas1, Caroline Bosch1, Gisela V Saborit1, Josep Bonjoch1, Ben Bradshaw1.   

Abstract

An unprecedented C-C coupling reaction between alkenes and ketones by hydrogen-atom transfer, using Fe(acac)3 and PhSiH3 in EtOH, is described. This mild protocol features high site selectivity and allows the construction of sterically congested structures containing tertiary alcohols and quaternary centers. The overall process introduces a novel strategic bond disconnection for ring-closing reactions.
© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  alkenes; cyclizations; iron; ketones; radicals

Year:  2017        PMID： 29115722     DOI： 10.1002/anie.201709659

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  6 in total

1.  Roles of Iron Complexes in Catalytic Radical Alkene Cross-Coupling: A Computational and Mechanistic Study.

Authors:  Dongyoung Kim; S M Wahidur Rahaman; Brandon Q Mercado; Rinaldo Poli; Patrick L Holland
Journal:  J Am Chem Soc       Date:  2019-04-26       Impact factor: 15.419

2.  Branch-Selective Addition of Unactivated Olefins into Imines and Aldehydes.

Authors:  Jeishla L M Matos; Suhelen Vásquez-Céspedes; Jieyu Gu; Takuya Oguma; Ryan A Shenvi
Journal:  J Am Chem Soc       Date:  2018-11-29       Impact factor: 15.419

3.  Catalytic Cycloisomerization onto a Carbonyl Oxygen.

Authors:  Shicheng Shi; Jonathan L Kuo; Tao Chen; Jack R Norton
Journal:  Org Lett       Date:  2020-07-22       Impact factor: 6.005

4.  Electroreductive Olefin-Ketone Coupling.

Authors:  Pengfei Hu; Byron K Peters; Christian A Malapit; Julien C Vantourout; Pan Wang; Jinjun Li; Lucas Mele; Pierre-Georges Echeverria; Shelley D Minteer; Phil S Baran
Journal:  J Am Chem Soc       Date:  2020-12-01       Impact factor: 15.419

5.  SOMOphilic Alkynylation of Unreactive Alkenes Enabled by Iron-Catalyzed Hydrogen Atom Transfer.

Authors:  Binlin Zhao; Tianxiang Zhu; Mengtao Ma; Zhuangzhi Shi
Journal:  Molecules       Date:  2021-12-22       Impact factor: 4.411

Review 6.  Methodologies for the synthesis of quaternary carbon centers via hydroalkylation of unactivated olefins: twenty years of advances.

Authors:  Thiago S Silva; Fernando Coelho
Journal:  Beilstein J Org Chem       Date:  2021-07-07       Impact factor: 2.883
  6 in total

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