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A Drastic Effect of TEMPO in Zinc‐Catalyzed Stannylation of Terminal Alkynes with Hydrostannanes via Dehydrogenation and Oxidative Dehydrogenation
Author(s) -
Kai Yuichi,
Oku Shinya,
Tani Tomohiro,
Sakurai Kyoko,
Tsuchimoto Teruhisa
Publication year - 2019
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201900540
Subject(s) - dehydrogenation , chemistry , catalysis , alkyne , zinc , nitrile , pyridine , oxidative addition , tin , combinatorial chemistry , lewis acids and bases , photochemistry , organic chemistry
Abstract With a system consisting of a catalytic zinc Lewis acid, pyridine, and TEMPO in a nitrile medium, terminal alkynes coupled with HSnBu 3 , 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 TEMPOSnBu 3 formed in situ from TEMPO and HSnBu 3 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.