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Transient‐Ligand‐Enabled ortho ‐Arylation of Five‐Membered Heterocycles: Facile Access to Mechanochromic Materials
Author(s) -
Li Bijin,
Seth Kapileswar,
Niu Ben,
Pan Lei,
Yang Huiwen,
Ge Haibo
Publication year - 2018
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201713357
Subject(s) - ligand (biochemistry) , aryl , transient (computer programming) , construct (python library) , combinatorial chemistry , coupling (piping) , chemistry , materials science , computer science , organic chemistry , alkyl , receptor , operating system , biochemistry , metallurgy , programming language
Reported herein is the first example of a direct arylation of heteroarenes by a transient‐ligand‐directed strategy without the need to construct and deconstruct the directing group. A wide range of heteroarenes undergoes the coupling with diverse aryl iodides to assemble a large library of highly selective and functionalized 3‐arylthiophene‐2‐carbaldehydes. This route provides an opportunity to rapidly access new mechanofluorochromic materials. Moreover, a novel strategy for mechanochromic luminogens with chromism trends of red‐ and blue‐shifts has been disclosed for the first time by facile functional‐group modifications to a common structural core.