Recent Advances in Functionalization of Pyrroles and their Translational Potential.
C−H functionalization
Pyrrole
Pyrrole derivatization
Journal
Chemical record (New York, N.Y.)
ISSN: 1528-0691
Titre abrégé: Chem Rec
Pays: United States
ID NLM: 101085550
Informations de publication
Date de publication:
Apr 2021
Apr 2021
Historique:
revised:
08
02
2021
received:
12
01
2021
accepted:
10
02
2021
pubmed:
3
3
2021
medline:
3
3
2021
entrez:
2
3
2021
Statut:
ppublish
Résumé
Among the known aromatic nitrogen heterocycles, pyrrole represents a privileged aromatic heterocycle ranging its occurrence in the key component of "pigments of life" to biologically active natural products to active pharmaceuticals. Pyrrole being an electron-rich heteroaromatic compound, its predominant functionalization is legendary to aromatic electrophilic substitution reactions. Although a few excellent reviews on the functionalization of pyrroles including the reports by Baltazzi in 1963, Casiraghi and Rassu in 1995, and Banwell in 2006 are available, they are fragmentary and over fifteen years old, and do not cover the modern aspects of catalysis. A review covering a comprehensive package of direct functionalization on pyrroles via catalytic and non-catalytic methods including their translational potential is described. Subsequent to statutory yet concise introduction, the classical functionalization on pyrroles using Lewis acids largely following an ionic mechanism is discussed. The subsequent discussion follows the various metal-catalyzed C-H functionalization on pyrroles, which are otherwise difficult to implement by Lewis acids. A major emphasize is given on the radical based pyrrole functionalization under metal-free oxidative conditions, which is otherwise poorly highlighted in the literature. Towards the end, the current development of pyrrole functionalization under photocatalyzed and electrochemical conditions is appended. Only a selected examples of substrates and important mechanisms are discussed for different methods highlighting their scopes and limitations. The aromatic nucleophillic substitution on pyrroles (being an electron-rich heterocycle) happened to be the subject of recent investigations, which has also been covered accentuating their underlying conceptual development. Despite great achievements over the past several years in these areas, many challenges and problems are yet to be solved, which are all discussed in summary and outlook.
Identifiants
pubmed: 33650751
doi: 10.1002/tcr.202100010
doi:
Types de publication
Journal Article
Review
Langues
eng
Sous-ensembles de citation
IM
Pagination
715-780Subventions
Organisme : CSIR
ID : 02(0337)/18/EMR-II
Informations de copyright
© 2021 The Chemical Society of Japan & Wiley-VCH GmbH.
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