Literature DB >> 22732723

Photochemical reactions of aromatic compounds and the concept of the photon as a traceless reagent.

Norbert Hoffmann1.   

Abstract

Electronic excitation significantly changes the reactivity of chemical compounds. Compared to ground state reactions, photochemical reactions considerably enlarge the application spectrum of a particular functional group in organic synthesis. Multistep syntheses may be simplified and perspectives for target oriented synthesis (TOS) and diversity oriented synthesis (DOS) are developed. New compound families become available or may be obtained more easily. In contrast to common chemical reagents, photons don't generate side products resulting from the transformation of a chemical reagent. Therefore, they are considered as a traceless reagent. Consequently, photochemical reactions play a central role in the methodology of sustainable chemistry. This aspect has been recognized since the beginning of the 20th century. As with many other photochemical transformations, photochemical reactions of aromatic, benzene-like compounds illustrate well the advantages in this context. Photochemical cycloadditions of aromatic compounds have been investigated for a long time. Currently, they are applied in various fields of organic synthesis. They are also studied in supramolecular structures. The phenomena of reactivity and stereoselectivity are investigated. During recent years, photochemical electron transfer mediated reactions are particularly focused. Such transformations have likewise been performed with aromatic compounds. Reactivity and selectivity as well as application to organic synthesis are studied.

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Year:  2012        PMID: 22732723     DOI: 10.1039/c2pp25074h

Source DB:  PubMed          Journal:  Photochem Photobiol Sci        ISSN: 1474-905X            Impact factor:   3.982


  15 in total

1.  Photoassisted Synthesis of Complex Molecular Architectures: Dearomatization of Benzenoid Arenes with Aza-o-xylylenes via an Unprecedented [2+4] Reaction Topology.

Authors:  Dmitry M Kuznetsov; Olga A Mukhina; Andrei G Kutateladze
Journal:  Angew Chem Int Ed Engl       Date:  2016-04-21       Impact factor: 15.336

2.  A Phosphine-Mediated Dearomative Skeletal Rearrangement of Dianiline Squaraine Dyes.

Authors:  Emily P Bacher; Kevin J Koh; Antonio J Lepore; Allen G Oliver; Olaf Wiest; Brandon L Ashfeld
Journal:  Org Lett       Date:  2021-03-26       Impact factor: 6.005

3.  Microflow photochemistry: UVC-induced [2 + 2]-photoadditions to furanone in a microcapillary reactor.

Authors:  Sylvestre Bachollet; Kimitada Terao; Shin Aida; Yasuhiro Nishiyama; Kiyomi Kakiuchi; Michael Oelgemöller
Journal:  Beilstein J Org Chem       Date:  2013-10-04       Impact factor: 2.883

Review 4.  Photochemical Approaches to Complex Chemotypes: Applications in Natural Product Synthesis.

Authors:  Markus D Kärkäs; John A Porco; Corey R J Stephenson
Journal:  Chem Rev       Date:  2016-04-27       Impact factor: 60.622

5.  Mechanisms and applications of cyclometalated Pt(ii) complexes in photoredox catalytic trifluoromethylation.

Authors:  Won Joon Choi; Sungkyu Choi; Kei Ohkubo; Shunichi Fukuzumi; Eun Jin Cho; Youngmin You
Journal:  Chem Sci       Date:  2014-11-24       Impact factor: 9.825

6.  Reversal of reaction type selectivity by Lewis acid coordination: the ortho photocycloaddition of 1- and 2-naphthaldehyde.

Authors:  Simone Stegbauer; Noah Jeremias; Christian Jandl; Thorsten Bach
Journal:  Chem Sci       Date:  2019-07-29       Impact factor: 9.825

7.  Photons as a 21st century reagent.

Authors:  Holly E Bonfield; Thomas Knauber; François Lévesque; Eric G Moschetta; Flavien Susanne; Lee J Edwards
Journal:  Nat Commun       Date:  2020-02-06       Impact factor: 14.919

8.  Multidimensional reaction screening for photochemical transformations as a tool for discovering new chemotypes.

Authors:  Véronique I Martin; John R Goodell; Oscar J Ingham; John A Porco; Aaron B Beeler
Journal:  J Org Chem       Date:  2014-04-16       Impact factor: 4.354

9.  Photochemical approach to functionalized benzobicyclo[3.2.1]octene structures via fused oxazoline derivatives from 4- and 5-(o-vinylstyryl)oxazoles.

Authors:  Ivana Sagud; Simona Božić; Zeljko Marinić; Marija Sindler-Kulyk
Journal:  Beilstein J Org Chem       Date:  2014-09-18       Impact factor: 2.883

10.  Enantioselective Lewis Acid Catalyzed ortho Photocycloaddition of Olefins to Phenanthrene-9-carboxaldehydes.

Authors:  Simone Stegbauer; Christian Jandl; Thorsten Bach
Journal:  Angew Chem Int Ed Engl       Date:  2018-10-05       Impact factor: 15.336

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