- PtCl4-catalyzed cyclization of N-acetyl-2-alkynylanilines: A mild and efficient synthesis of N-acetyl-2-substituted indoles
-
An efficient synthesis of N-acetyl-2-substituted indole derivatives via direct intramolecular hydroamination of N-acetyl-2-alkynylaniline derivatives was developed. The reaction could be applied to a wide range of substrates employing only 1–2 mol% of PtCl4 as the catalyst to furnish the desired indole products in moderate to excellent yields. The current protocol is efficient, reliable and scalable, and could serve as an important tool for convenient and rapid access to this important class of N-heterocyclic skeleton from readily available substrates.
- Chaisan, Nattawadee,Kaewsri, Wilailak,Thongsornkleeb, Charnsak,Tummatorn, Jumreang,Ruchirawat, Somsak
-
supporting information
p. 675 - 680
(2018/01/18)
-
- Cobalt(II)-catalyzed regioselective C-H halogenation of anilides
-
A cobalt-catalyzed regioselective C-H halogenation methodology is reported herein. The highlight of this work is the highly selective C-H functionalization of anilides, which results in high-yielding, versatile, and practical halogenated products. Thereby, brominations, chlorinations and iodinations of many electron-rich and electron-deficient anilides were achieved in a highly selective fashion. Mechanistic studies with respect to the pathway of the reaction are also described.
- Li, Ze-lin,Sun, Kang-kang,Cai, Chun
-
supporting information
p. 5433 - 5440
(2018/08/12)
-
- Palladium-Catalyzed, ortho-Selective C-H Halogenation of Benzyl Nitriles, Aryl Weinreb Amides, and Anilides
-
A palladium-catalyzed, ortho-selective C-H halogenation methodology is reported herein. The highlight of the work is the highly selective C(sp2)-H functionalization of benzyl nitriles in the presence of activated C(sp3)-H bond, which results in good yields of the halogenated products with excellent regioselectivity. Along with benzyl nitriles, aryl Weinreb amides and anilides have been evaluated for the transformation using aprotic conditions. Mechanistic studies yield interesting aspects with respect to the pathway of the reaction and the directing group abilities.
- Das, Riki,Kapur, Manmohan
-
p. 1114 - 1126
(2018/06/18)
-
- Monoprotected l-Amino Acid (l-MPAA), Accelerated Bromination, Chlorination, and Iodination of C(sp2)?H Bonds by Iridium(III) Catalysis
-
Halogenated arenes are important structural motifs commonly found in biologically active molecules and used for a variety of transformations in organic synthesis. Herein, we report the mono-protected l-amino acid (l-MPAA) accelerated iridium(III)-catalyzed halogenation of (hetero)anilides at room temperature. This reaction constitutes the first example of an iridium(III)/l-MPAA-catalyzed general halogenation of (hetero)arenes through C(sp2)?H activation. Furthermore, we demonstrate the potential utility of our method through its use in the synthesis of a quinolone derivative.
- Kathiravan, Subban,Nicholls, Ian A.
-
supporting information
p. 7031 - 7036
(2017/05/29)
-
- Synthesis of 2,3-Disubstituted Indoles and Benzofurans by the Tandem Reaction of Rhodium(II)-Catalyzed Intramolecular C-H Insertion and Oxygen-Mediated Oxidation
-
A highly effective and straightforward method to construct a wide range of functionalized 2,3-disubstituted indoles has been developed. The method involves the tandem reaction of rhodium(II)-catalyzed denitrogenative annulation of triazole-based benzyl an
- Shen, Hongjuan,Fu, Junkai,Yuan, Hao,Gong, Jianxian,Yang, Zhen
-
p. 10180 - 10192
(2016/11/17)
-
- Synthesis and structural insights of substituted 2-iodoacetanilides and 2-iodoanilines
-
This study reports a simple and efficient method for the direct iodination of substituted anilines with molecular iodine and copper acetate in acetic acid producing 2-iodoacetanilies and 2-iodoanilines. Employing density functional theory (B3LYP) and MidiX basis set, computational study is performed to calculate equilibrium geometries, IR vibrational frequencies, and thermodynamic properties including change of energy, enthalpy and Gibbs free energies. The optimized geometries indicated longer C-I bond distance (2.133 ?) which makes iodine slightly positive. The partial atomic charge profile and electrostatic potential further confirmed that most of the iodinated products are capable of forming a distinct halogen bonding . The thermodynamic properties disclosed that all iodination reactions are endothermic. Understanding the substituents' effect, molecular frontier orbital (MO) calculations are conducted finding the HOMO, LUMO and HOMO-LUMO gaps for all compounds. The MO calculations revealed that two electron-withdrawing iodine groups have significant influence on lowering the HOMO-LUMO gap compared to one iodine group in the products.
- Hoque, Mohammad Mazharol,Halim, Mohammad A.,Rahman, Mohammad Mizanur,Hossain, Mohammad Ismail,Khan, Md. Wahab
-
p. 367 - 374
(2013/11/19)
-
- Design and synthesis of 1-benzazepine derivatives by strategic utilization of Suzuki-Miyaura cross-coupling, aza-Claisen rearrangement and ring-closing metathesis
-
A new and simple methodology has been realized for the synthesis of 7-substituted 2,3,4,5-tetrahydro-1-benzazepine derivatives with Suzuki-Miyaura cross-coupling, aza-Claisen rearrangement and ring-closing metathesis (RCM) the key steps. Here, o-allylacet
- Kotha, Sambasivarao,Shah, Vrajesh R.
-
experimental part
p. 1054 - 1064
(2009/04/05)
-
- Oxidative Iodination of Aromatic Amides Using Sodium Perborate or Hydrogen Peroxide with Sodium Tungstate
-
Hydrogen peroxide or sodium perborate in the presence of a sodium tungstate catalyst are shown to be cheap oxidants for the iodination of aromatic amides using potassium iodide as the source of the iodine.
- Beinker, Philipp,Hanson, James R.,Meindl, Nadja,Rodriguez Medina, Inmaculada C.
-
p. 204 - 205
(2007/10/03)
-
- A Novel Aromatic Iodination Method Using F2
-
A new method for direct aromatic iodination with IF, made in situ from the corresponding elements, is described.Depending on the reaction time and temperature, mono- or polyiodination can be achieved.Even deactivated aromatic rings can be directly iodinated without the presence of any Friedel-Crafts catalyst.Sensitive groups such as aromatic aldehydes are not affected by the reagent.
- Rozen, Shlomo,Zamir, Dov
-
p. 3552 - 3555
(2007/10/02)
-