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Cover Feature: Coupling‐Isomerization‐Cycloisomerization Reaction (CICIR) – An Unexpected and Efficient Domino Approach to Luminescent 2‐(Hydroxymethylene)indenones (Eur. J. Org. Chem. 42/2019)
Author(s) -
Ghazvini Helya Janatian,
Armaghan Mahsa,
Janiak Christoph,
Balalaie Saeed,
Müller Thomas J. J.
Publication year - 2019
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201901546
Subject(s) - cycloisomerization , chemistry , isomerization , domino , intramolecular force , aryl , photochemistry , sonogashira coupling , propargyl , cascade reaction , luminescence , combinatorial chemistry , palladium , catalysis , stereochemistry , organic chemistry , optoelectronics , alkyl , physics
The Cover Feature shows that like a Ferris wheel a domino process catalyzed by palladium and copper complexes and DBU as a base transforms ortho ‐halo (hetero)aryl carboxaldehydes and propargyl alcohols into 2‐(hydroxymethylene)indenones in very good to excellent yield. According to control experiments, this novel coupling–isomerization–cycloisomerization reaction (CICIR) concatenates Sonogashira alkynylation–isomerization followed by intramolecular carbonyl‐ene‐type reaction and concluded by a base mediated conducted‐tour 1,3‐H shift. The resulting luminophores with tunable emission solvatochromicity make the fair adventure complete. More information can be found in the Communication by S. Balalaie, T. J. J. Müller et al.