Literature DB >> 31850410

Photoinduced deaminative strategies: Katritzky salts as alkyl radical precursors.

José Tiago M Correia1, Vitor A Fernandes1, Bianca T Matsuo1, José A C Delgado1, Wanderson C de Souza1, Márcio Weber Paixão1.   

Abstract

Primary amines are one of the most predominant functional groups found in organic molecules. These entities help form the chemical architecture of natural products, bioactive molecules, synthetic building blocks and catalysts. Due to their ubiquitous presence, the development of strategies for the construction of C-C or C-X bonds through deaminative processes is of high importance. Deaminative methods offer new possibilities on the retrosynthetic rationale, and enable late-stage-functionalization of complex structures. As a result of the recent development of photoinduced processes, a variety of photo-mediated deaminative protocols employing 2,4,6-triphenyl-pyridinium salts - Katritzky Salts - as activating agents have been recently realized. This review covers the most recent developments of deaminative strategies by using Katritzky Salts as alkyl radical reservoirs, with particular concern on photoinduced processes applied to organic synthesis.

Entities:  

Year:  2019        PMID: 31850410     DOI: 10.1039/c9cc08348k

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN: 1359-7345            Impact factor:   6.222


  13 in total

1.  Tunable and Practical Homogeneous Organic Reductants for Cross-Electrophile Coupling.

Authors:  David J Charboneau; Haotian Huang; Emily L Barth; Cameron C Germe; Nilay Hazari; Brandon Q Mercado; Mycah R Uehling; Susan L Zultanski
Journal:  J Am Chem Soc       Date:  2021-11-30       Impact factor: 15.419

2.  Dual Nickel/Photoredox-Catalyzed Deaminative Cross-Coupling of Sterically Hindered Primary Amines.

Authors:  Julia R Dorsheimer; Melissa A Ashley; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2021-11-12       Impact factor: 15.419

3.  Continuous-Flow Synthesis of Pyrylium Tetrafluoroborates: Application to Synthesis of Katritzky Salts and Photoinduced Cationic RAFT Polymerization.

Authors:  Carlo Sambiagio; Matteo Ferrari; Koen van Beurden; Nicola Della Ca'; Jack van Schijndel; Timothy Noël
Journal:  Org Lett       Date:  2021-03-02       Impact factor: 6.005

Review 4.  Leveraging of Sulfur Anions in Photoinduced Molecular Transformations.

Authors:  Haoyu Li; Yuliang Liu; Shunsuke Chiba
Journal:  JACS Au       Date:  2021-10-20

5.  Visible-light-mediated catalyst-free synthesis of unnatural α-amino acids and peptide macrocycles.

Authors:  Mengran Wang; Chao Wang; Yumei Huo; Xiaobo Dang; Hongxiang Xue; Liangyu Liu; Hongli Chai; Xiuling Xie; Zhixuan Li; Doudou Lu; Zhaoqing Xu
Journal:  Nat Commun       Date:  2021-11-25       Impact factor: 14.919

6.  Direct access to tetrasubstituted cyclopentenyl scaffolds through a diastereoselective isocyanide-based multicomponent reaction.

Authors:  Vitor A Fernandes; Rafaely N Lima; Yoisel B Broterson; Meire Y Kawamura; Radell Echemendía; Alexander F de la Torre; Marco A B Ferreira; Daniel G Rivera; Marcio W Paixão
Journal:  Chem Sci       Date:  2021-09-16       Impact factor: 9.825

7.  Regioselective C-3-alkylation of quinoxalin-2(1H)-ones via C-N bond cleavage of amine derived Katritzky salts enabled by continuous-flow photoredox catalysis.

Authors:  Gandhari Kishor; Vankudoth Ramesh; Vadithya Ranga Rao; Srihari Pabbaraja; Praveen Reddy Adiyala
Journal:  RSC Adv       Date:  2022-04-29       Impact factor: 4.036

8.  A donor-acceptor complex enables the synthesis of E-olefins from alcohols, amines and carboxylic acids.

Authors:  Kun-Quan Chen; Jie Shen; Zhi-Xiang Wang; Xiang-Yu Chen
Journal:  Chem Sci       Date:  2021-04-05       Impact factor: 9.825

9.  Phosphite mediated asymmetric N to C migration for the synthesis of chiral heterocycles from primary amines.

Authors:  Soniya Rani; Soumya Ranjan Dash; Asish Bera; Md Nirshad Alam; Kumar Vanka; Pradip Maity
Journal:  Chem Sci       Date:  2021-05-28       Impact factor: 9.825

10.  Photocatalytic deaminative benzylation and alkylation of tetrahydroisoquinolines with N-alkylpyrydinium salts.

Authors:  David Schönbauer; Carlo Sambiagio; Timothy Noël; Michael Schnürch
Journal:  Beilstein J Org Chem       Date:  2020-04-21       Impact factor: 2.883

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