Literature DB >> 29266582

α-Aminoxy-Acid-Auxiliary-Enabled Intermolecular Radical γ-C(sp3 )-H Functionalization of Ketones.

Heng Jiang1, Armido Studer1.   

Abstract

A method for site-specific intermolecular γ-C(sp3 )-H functionalization of ketones has been developed using an α-aminoxy acid auxiliary applying photoredox catalysis. Regioselective activation of an inert C-H bond is achieved by 1,5-hydrogen atom abstraction by an oxidatively generated iminyl radical. Tertiary and secondary C-radicals thus formed at the γ-position of the imine functionality undergo radical conjugate addition to various Michael acceptors to provide, after reduction and imine hydrolysis, the corresponding γ-functionalized ketones.
© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  C−H bond functionalization; iminyl radical; ketone; photoredox chemistry; redox-neutral

Year:  2018        PMID： 29266582     DOI： 10.1002/anie.201712066

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


  21 in total

1.  Sulfamate Esters Guide C(3)-Selective Xanthylation of Alkanes.

Authors:  Suraj K Ayer; J L Roizen
Journal:  J Org Chem       Date:  2019-02-26       Impact factor: 4.354

2.  Aliphatic Radical Relay Heck Reaction at Unactivated C(sp3 )-H Sites of Alcohols.

Authors:  Padon Chuentragool; Dongari Yadagiri; Taiki Morita; Sumon Sarkar; Marvin Parasram; Yang Wang; Vladimir Gevorgyan
Journal:  Angew Chem Int Ed Engl       Date:  2019-01-17       Impact factor: 15.336

3.  Catalytic Alkene Difunctionalization via Imidate Radicals.

Authors:  Kohki M Nakafuku; Stacy C Fosu; David A Nagib
Journal:  J Am Chem Soc       Date:  2018-08-29       Impact factor: 15.419

4.  δ-C-H Mono- and Dihalogenation of Alcohols.

Authors:  Alastair N Herron; Dongxin Liu; Guoqin Xia; Jin-Quan Yu
Journal:  J Am Chem Soc       Date:  2020-01-30       Impact factor: 15.419

Review 5.  Strategies to Generate Nitrogen-centered Radicals That May Rely on Photoredox Catalysis: Development in Reaction Methodology and Applications in Organic Synthesis.

Authors:  Kitae Kwon; R Thomas Simons; Meganathan Nandakumar; Jennifer L Roizen
Journal:  Chem Rev       Date:  2021-10-08       Impact factor: 60.622

6.  Remote C-H Functionalization via Selective Hydrogen Atom Transfer.

Authors:  Leah M Stateman; Kohki M Nakafuku; David A Nagib
Journal:  Synthesis (Stuttg)       Date:  2018-02-12       Impact factor: 3.157

7.  Ligand-Enabled γ-C(sp3)-H Activation of Ketones.

Authors:  Ru-Yi Zhu; Zi-Qi Li; Han Seul Park; Chris H Senanayake; Jin-Quan Yu
Journal:  J Am Chem Soc       Date:  2018-03-02       Impact factor: 15.419

8.  Radical cascade synthesis of azoles via tandem hydrogen atom transfer.

Authors:  Andrew D Chen; James H Herbort; Ethan A Wappes; Kohki M Nakafuku; Darsheed N Mustafa; David A Nagib
Journal:  Chem Sci       Date:  2020-01-31       Impact factor: 9.825

Review 9.  Photoredox-Catalyzed C-H Functionalization Reactions.

Authors:  Natalie Holmberg-Douglas; David A Nicewicz
Journal:  Chem Rev       Date:  2021-09-29       Impact factor: 60.622

Review 10.  Recent Advances in Photoredox-Mediated Radical Conjugate Addition Reactions: An Expanding Toolkit for the Giese Reaction.

Authors:  Anastasia L Gant Kanegusuku; Jennifer L Roizen
Journal:  Angew Chem Int Ed Engl       Date:  2021-07-21       Impact factor: 16.823
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