Literature DB >> 30986072

PIFA-Promoted, Solvent-Controlled Selective Functionalization of C(sp2)-H or C(sp3)-H: Nitration via C-N Bond Cleavage of CH3NO2, Cyanation, or Oxygenation in Water.

Chandrashekar Mudithanapelli1, Lama Prema Dhorma1, Mi-Hyun Kim1.   

Abstract

A novel nitration (via C(sp3)-N breaking/C(sp2)-N formation with CH3NO2) mediated by [bis(trifluoroacetoxy)iodo]benzene (PIFA) is described. The NO2 transfer from CH3NO2 to the aromatic group of the substrate is possible with careful selection of the solvent, NaX, and oxidant. In addition, the solvent-controlled C(sp2)-H functionalization can shift to an α-C(sp3)-H functionalization (cyanation or oxygenation) of the α-C(sp3)-H of cyclic amines.

Entities:  

Year:  2019        PMID： 30986072     DOI： 10.1021/acs.orglett.9b00751

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


  5 in total

1.  Regioselective α-Cyanation of Unprotected Alicyclic Amines.

Authors:  Fuchao Yu; Daniel A Valles; Weijie Chen; Scott D Daniel; Ion Ghiviriga; Daniel Seidel
Journal:  Org Lett       Date:  2022-08-29       Impact factor: 6.072

2.  Design, Synthesis, and Monoamine Oxidase B Selective Inhibitory Activity of N-Arylated Heliamine Analogues.

Authors:  Makito Yamada; Yu Hirose; Bangzhong Lin; Megumi Fumimoto; Kazuto Nunomura; Sirimangkalakitti Natchanun; Naoyuki Takahashi; Yuuta Ohki; Makoto Sako; Kenichi Murai; Kazuo Harada; Masayoshi Arai; Sayo Suzuki; Tomonori Nakamura; Junichi Haruta; Mitsuhiro Arisawa
Journal:  ACS Med Chem Lett       Date:  2022-08-22       Impact factor: 4.632

3.  Positioning of an unprecedented spiro[5.5]undeca ring system into kinase inhibitor space.

Authors:  Arramshetti Venkanna; Lalita Subedi; Mahesh K Teli; Prema Dhorma Lama; Bhargav Gupta Nangunuri; Sang-Yoon Lee; Sun Yeou Kim; Mi-Hyun Kim
Journal:  Sci Rep       Date:  2020-12-04       Impact factor: 4.379

4.  Copper(II)-Dioxygen Facilitated Activation of Nitromethane: Nitrogen Donors for the Synthesis of Substituted 2-Hydroxyimino-2-phenylacetonitriles and Phthalimides.

Authors:  Shiqun Xiang; Yinghua Li; Weibin Fan; Jiang Jin; Wei Zhang; Deguang Huang
Journal:  Front Chem       Date:  2021-01-29       Impact factor: 5.221

5.  Copper catalyzed late-stage C(sp3)-H functionalization of nitrogen heterocycles.

Authors:  Zhe Chang; Jialin Huang; Si Wang; Geshuyi Chen; Heng Zhao; Rui Wang; Depeng Zhao
Journal:  Nat Commun       Date:  2021-07-15       Impact factor: 14.919
  5 in total

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