Literature DB >> 23055443

Modular synthesis of phenanthridine derivatives by oxidative cyclization of 2-isocyanobiphenyls with organoboron reagents.

Mamoru Tobisu1, Keika Koh, Takayuki Furukawa, Naoto Chatani.   

Abstract

Where HAS you been? A manganese-mediated annulation of 2-isocyanobiaryls with organoboronic acids is developed for the synthesis of a broad range of phenanthridine derivatives. Mechanistic studies indicate that the reaction proceeds by the intramolecular homolytic aromatic substitution (HAS) of an imidoyl radical intermediate.
Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Year:  2012        PMID: 23055443     DOI: 10.1002/anie.201206115

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


  10 in total

1.  Access to 1-amino-3,4-dihydroisoquinolines via palladium-catalyzed C-H bond aminoimidoylation reaction from functionalized isocyanides.

Authors:  Zhuang Xiong; Panyuan Cai; Yingshuang Mei; Jian Wang
Journal:  RSC Adv       Date:  2019-12-18       Impact factor: 4.036

2.  Expanding the palette of phenanthridinium cations.

Authors:  Andrew G Cairns; Hans Martin Senn; Michael P Murphy; Richard C Hartley
Journal:  Chemistry       Date:  2014-03-24       Impact factor: 5.236

Review 3.  Come-back of phenanthridine and phenanthridinium derivatives in the 21st century.

Authors:  Lidija-Marija Tumir; Marijana Radić Stojković; Ivo Piantanida
Journal:  Beilstein J Org Chem       Date:  2014-12-10       Impact factor: 2.883

Review 4.  A lesson for site-selective C-H functionalization on 2-pyridones: radical, organometallic, directing group and steric controls.

Authors:  Koji Hirano; Masahiro Miura
Journal:  Chem Sci       Date:  2017-11-27       Impact factor: 9.825

5.  Oxidative Photocyclization of Aromatic Schiff Bases in Synthesis of Phenanthridines and Other Aza-PAHs.

Authors:  Martin Kos; Jaroslav Žádný; Jan Storch; Vladimír Církva; Petra Cuřínová; Jan Sýkora; Ivana Císařová; Febin Kuriakose; Igor V Alabugin
Journal:  Int J Mol Sci       Date:  2020-08-15       Impact factor: 5.923

6.  Phenanthrenequinone-Sensitized Photocatalytic Synthesis of Polysubstituted Quinolines from 2-Vinylarylimines.

Authors:  Juulia Talvitie; Iida Alanko; Evgeny Bulatov; Juho Koivula; Topias Pöllänen; Juho Helaja
Journal:  Org Lett       Date:  2021-12-20       Impact factor: 6.005

7.  PPh3/NaI driven photocatalytic decarboxylative radical cascade alkylarylation reaction of 2-isocyanobiaryls.

Authors:  Ketan Wadekar; Suraj Aswale; Veera Reddy Yatham
Journal:  RSC Adv       Date:  2020-04-25       Impact factor: 4.036

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

9.  Synthesis of phenanthridines via palladium-catalyzed picolinamide-directed sequential C-H functionalization.

Authors:  Ryan Pearson; Shuyu Zhang; Gang He; Nicola Edwards; Gong Chen
Journal:  Beilstein J Org Chem       Date:  2013-05-08       Impact factor: 2.883

10.  Installing amino acids and peptides on N-heterocycles under visible-light assistance.

Authors:  Yunhe Jin; Min Jiang; Hui Wang; Hua Fu
Journal:  Sci Rep       Date:  2016-02-02       Impact factor: 4.379

  10 in total

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