Literature DB >> 26239615

Metal-Free Oxidative C-C Bond Formation through C-H Bond Functionalization.

Rishikesh Narayan1, Kiran Matcha1,2, Andrey P Antonchick3,4.   

Abstract

The formation of C-C bonds embodies the core of organic chemistry because of its fundamental application in generation of molecular diversity and complexity. C-C bond-forming reactions are well-known challenges. To achieve this goal through direct functionalization of C-H bonds in both of the coupling partners represents the state-of-the-art in organic synthesis. Oxidative C-C bond formation obviates the need for prefunctionalization of both substrates. This Minireview is dedicated to the field of C-C bond-forming reactions through direct C-H bond functionalization under completely metal-free oxidative conditions. Selected important developments in this area have been summarized with representative examples and discussions on their reaction mechanisms.
© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  CC coupling; CH activation; hypervalent iodine; metal-free; oxidative coupling

Year:  2015        PMID: 26239615     DOI: 10.1002/chem.201502005

Source DB:  PubMed          Journal:  Chemistry        ISSN: 0947-6539            Impact factor:   5.236


  8 in total

1.  N-Hydroxybenzimidazole as a structurally modifiable platform for N-oxyl radicals for direct C-H functionalization reactions.

Authors:  Tomomi Yoshii; Saori Tsuzuki; Shunya Sakurai; Ryu Sakamoto; Julong Jiang; Miho Hatanaka; Akira Matsumoto; Keiji Maruoka
Journal:  Chem Sci       Date:  2020-05-18       Impact factor: 9.825

2.  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

3.  N-Heterocyclic carbene-catalyzed oxidative [3 + 2] annulation of dioxindoles and enals: cross coupling of homoenolate and enolate.

Authors:  Xiang-Yu Chen; Kun-Quan Chen; De-Qun Sun; Song Ye
Journal:  Chem Sci       Date:  2016-11-09       Impact factor: 9.825

4.  Metal-Free α-C(sp³)-H Functionalized Oxidative Cyclization of Tertiary N,N-Diaryl Amino Alcohols: Theoretical Approach for Mechanistic Pathway.

Authors:  Zakir Ullah; Mihyun Kim
Journal:  Molecules       Date:  2017-03-29       Impact factor: 4.411

5.  Selective carboxylation of reactive benzylic C-H bonds by a hypervalent iodine(III)/inorganic bromide oxidation system.

Authors:  Toshifumi Dohi; Shohei Ueda; Kosuke Iwasaki; Yusuke Tsunoda; Koji Morimoto; Yasuyuki Kita
Journal:  Beilstein J Org Chem       Date:  2018-05-16       Impact factor: 2.883

6.  [1,5]-Hydride Shift-Cyclization versus C(sp2)-H Functionalization in the Knoevenagel-Cyclization Domino Reactions of 1,4- and 1,5-Benzoxazepines.

Authors:  Dóra Szalóki Vargáné; László Tóth; Balázs Buglyó; Attila Kiss-Szikszai; Attila Mándi; Péter Mátyus; Sándor Antus; Yinghan Chen; Dehai Li; Lingxue Tao; Haiyan Zhang; Tibor Kurtán
Journal:  Molecules       Date:  2020-03-11       Impact factor: 4.411

7.  Synthesis of N-alkoxyphthalimide derivatives via PIDA-promoted cross dehydrogenative coupling reaction.

Authors:  Rongxiang Chen; Bing Liu; Wenbo Li; Kai-Kai Wang; Changqing Miao; Zhizhuang Li; Yingjie Lv; Lantao Liu
Journal:  RSC Adv       Date:  2021-02-19       Impact factor: 3.361

8.  Metal-free oxidative isocyanides insertion with aromatic aldehydes to aroylated N-heterocycles.

Authors:  Yimiao He; Xuelian Wang; Jun-An Xiao; Jinying Pang; Chunfang Gan; Yanmin Huang; Chusheng Huang
Journal:  RSC Adv       Date:  2018-01-15       Impact factor: 3.361

  8 in total

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