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submitted on 22.05.2019 and posted on 24.05.2019by Tristan Delcaillau, Alessandro Bismuto, Zhong Lian, Bill Morandi
A nickel-catalyzed carbon-sulfur bond 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.
Further, synthetically challenging macrocycles could be obtained in good yield in
an unusual example of ring-closing metathesis which does not involve alkene
bonds. In-depth organometallic studies support a reversible Ni(0)-Ni(II)
pathway to product formation. Overall, this work does not only disclose a more
sustainable and more functional group tolerant alternative to previous catalytic
systems based on Pd, but also presents new applications and mechanistic
information which are highly relevant to the further development and
application of unusual single bond metathesis reactions.