Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 361, Issue 18, Pages 4314-4323Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201900540
Keywords
Alkynes; Dehydrogenation; Lewis acids; Tin; Zinc
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With a system consisting of a catalytic zinc Lewis acid, pyridine, and TEMPO in a nitrile medium, terminal alkynes coupled with HSnBu3, providing alkynylstannanes with structural diversity. The resulting alkynylstannane, without being isolated, could be directly used for Pd- and Cu-catalyzed transformations to deliver internal alkynes and more intricate tin-atom-containing molecules. Mechanistic studies indicated that TEMPOSnBu3 formed in situ from TEMPO and HSnBu3 works to stannylate the terminal alkyne in collaboration with the zinc catalyst, and that both of dehydrogenation and oxidative dehydrogenation processes are uniquely involved in a single reaction.
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