Literature DB >> 21286642

Direct Sp3α-C-H activation and functionalization of alcohol and ether.

Shu-Yu Zhang1, Fu-Min Zhang, Yong-Qiang Tu.   

Abstract

Seven kinds of sp(3)α-C-H activation/C-C formation reactions of alcohols and ethers have been reviewed in this tutorial review, from the viewpoint of both methodology and synthetic application, towards the efficiency, chemo-, regio- and stereoselectivity, catalytic system, substrate scope and mechanistic study. Section 2 describes radical-mediated α-C-H activation and addition/elimination of ethers with unsaturated (C=C and C[triple bond]C) species. Sections 3-8 discuss the α-C-H activation and additions of alcohols and/or ethers with unsaturated (C=C, C[triple bond]C, C=O and C=N) compounds, which involve the key processes of radical mediation, carbenoid insertion, 1,5-H-migration, oxidative dehydrogenation coupling, transfer hydrogenative coupling, and metal-mediated C=C insertion into the C-H bond.

Entities:  

Year:  2011        PMID: 21286642     DOI: 10.1039/c0cs00063a

Source DB:  PubMed          Journal:  Chem Soc Rev        ISSN: 0306-0012            Impact factor:   54.564


  27 in total

1.  Traceless Silylation of β-C(sp3)-H Bonds of Alcohols via Perfluorinated Acetals.

Authors:  Ala Bunescu; Trevor W Butcher; John F Hartwig
Journal:  J Am Chem Soc       Date:  2018-01-19       Impact factor: 15.419

2.  Catalytic Enantioselective Carbonyl Allylation and Propargylation via Alcohol-Mediated Hydrogen Transfer: Merging the Chemistry of Grignard and Sabatier.

Authors:  Seung Wook Kim; Wandi Zhang; Michael J Krische
Journal:  Acc Chem Res       Date:  2017-08-09       Impact factor: 22.384

3.  Direct α-arylation of ethers through the combination of photoredox-mediated C-H functionalization and the Minisci reaction.

Authors:  Jian Jin; David W C MacMillan
Journal:  Angew Chem Int Ed Engl       Date:  2014-12-02       Impact factor: 15.336

4.  Metal-free C(sp(3))-H functionalization: oxidative carbo-oxygenation of α-diazo carbonyls via radical dediazotization.

Authors:  Nan-Nan Wang; Wen-Juan Hao; Tian-Shu Zhang; Guigen Li; Ya-Nan Wu; Shu-Jiang Tu; Bo Jiang
Journal:  Chem Commun (Camb)       Date:  2016-03-21       Impact factor: 6.222

Review 5.  Catalytic enantioselective C-H functionalization of alcohols by redox-triggered carbonyl addition: borrowing hydrogen, returning carbon.

Authors:  John M Ketcham; Inji Shin; T Patrick Montgomery; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2014-07-23       Impact factor: 15.336

6.  The past, present, and future of the Yang reaction.

Authors:  Chuo Chen
Journal:  Org Biomol Chem       Date:  2016-08-12       Impact factor: 3.876

7.  Copper-catalyzed oxidative cross-dehydrogenative coupling of 2H-chromenes and terminal alkynes.

Authors:  Fei Yang; Yangshan Li; Paul E Floreancig; Xiaoyan Li; Lei Liu
Journal:  Org Biomol Chem       Date:  2018-07-18       Impact factor: 3.876

8.  The combined C-H functionalization/Cope rearrangement: discovery and applications in organic synthesis.

Authors:  Huw M L Davies; Yajing Lian
Journal:  Acc Chem Res       Date:  2012-05-11       Impact factor: 22.384

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

10.  Cross-dehydrogenative coupling and oxidative-amination reactions of ethers and alcohols with aromatics and heteroaromatics.

Authors:  Mahesh K Lakshman; Prasanna K Vuram
Journal:  Chem Sci       Date:  2017-06-30       Impact factor: 9.825

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