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Nickel‐Catalyzed Inter‐ and Intramolecular Aryl Thioether Metathesis by Reversible Arylation
Author(s) -
Delcaillau Tristan,
Bismuto Alessandro,
Lian Zhong,
Morandi Bill
Publication year - 2020
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.201910436
Subject(s) - thioether , metathesis , intramolecular force , aryl , alkene , catalysis , nickel , salt metathesis reaction , combinatorial chemistry , ring closing metathesis , chemistry , yield (engineering) , organic chemistry , materials science , polymerization , alkyl , metallurgy , polymer
A nickel‐catalyzed aryl thioether metathesis has been developed to access high‐value thioethers. 1,2‐Bis(dicyclohexylphosphino)ethane (dcype) is essential to promote this highly functional‐group‐tolerant reaction. Furthermore, synthetically challenging macrocycles could be obtained in good yield in an unusual example of ring‐closing metathesis that does not involve alkene bonds. In‐depth organometallic studies support a reversible Ni 0 /Ni II pathway to product formation. Overall, this work not only provides a more sustainable alternative to previous catalytic systems based on Pd, but also presents new applications and mechanistic information that are highly relevant to the further development and application of unusual single‐bond metathesis reactions.