Literature DB >> 29424047

Halogen Bond Catalyzed Bromocarbocyclization.

Yuk-Cheung Chan1, Ying-Yeung Yeung1.   

Abstract

A halogen bond catalyzed bromo-carbocyclization of N-cinnamyl sulfonamides and O-cinnamyl phenyl ethers has been developed. N-methyl 4-iodopyridinium triflate is used as the halogen-bonding organocatalyst and the reaction is highly chemoselective. This report represents the first proof-of-concept for halogen-bonding organocatalyst-promoted electrophilic halogenation. Mechanistic study suggests the autocatalytic nature of this reaction.
© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  cyclization; halogens; heterocycles; organocatalysis; reaction mechanisms

Year:  2018        PMID： 29424047     DOI： 10.1002/anie.201800261

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


  8 in total

1.  Pnictogen, chalcogen, and halogen bonds in catalytic systems: theoretical study and detailed comparison.

Authors:  Ling Lu; Yunxiang Lu; Zhengdan Zhu; Honglai Liu
Journal:  J Mol Model       Date:  2019-12-20       Impact factor: 1.810

2.  Synthesis of Enantioenriched 3,4-Disubstituted Chromans through Lewis Base Catalyzed Carbosulfenylation.

Authors:  Travis Menard; Aragorn Laverny; Scott E Denmark
Journal:  J Org Chem       Date:  2021-10-21       Impact factor: 4.354

3.  Association of Halogen Bonding and Hydrogen Bonding in Metal Acetate-Catalyzed Asymmetric Halolactonization.

Authors:  Takayoshi Arai; Kodai Horigane; Ohji Watanabe; Junki Kakino; Noriyuki Sugiyama; Hiroki Makino; Yuto Kamei; Shinnosuke Yabe; Masahiro Yamanaka
Journal:  iScience       Date:  2019-01-23

4.  Chalcogen bond-guided conformational isomerization enables catalytic dynamic kinetic resolution of sulfoxides.

Authors:  Jianjian Liu; Mali Zhou; Rui Deng; Pengcheng Zheng; Yonggui Robin Chi
Journal:  Nat Commun       Date:  2022-08-15       Impact factor: 17.694

5.  Highly Selective and Catalytic C-N Bond Cleavage of Tertiary Sulfonamides: Scope and Mechanistic Insight.

Authors:  Aditya Bhattacharya; Pushpendra Mani Shukla; Biswajit Maji
Journal:  ACS Omega       Date:  2021-07-16

Review 6.  Application of Halogen Bonding to Organocatalysis: A Theoretical Perspective.

Authors:  Hui Yang; Ming Wah Wong
Journal:  Molecules       Date:  2020-02-26       Impact factor: 4.411

Review 7.  A Halogen Bonding Perspective on Iodothyronine Deiodinase Activity.

Authors:  Eric S Marsan; Craig A Bayse
Journal:  Molecules       Date:  2020-03-14       Impact factor: 4.411

8.  Intramolecular Povarov Reactions for the Synthesis of Chromenopyridine Fused 2-Pyridone Polyheterocycles Binding to α-Synuclein and Amyloid-β Fibrils.

Authors:  Dan E Adolfsson; Mohit Tyagi; Pardeep Singh; Adrian Deuschmann; Jörgen Ådén; Anna L Gharibyan; Sanduni Wasana Jayaweera; Anders E G Lindgren; Anders Olofsson; Fredrik Almqvist
Journal:  J Org Chem       Date:  2020-10-25       Impact factor: 4.354
  8 in total

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