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Cyclization of Gold Acetylides: Synthesis of Vinyl Sulfonates via Gold Vinylidene Complexes
Author(s) -
Bucher Janina,
Wurm Thomas,
Nalivela Kumara Swamy,
Rudolph Matthias,
Rominger Frank,
Hashmi A. Stephen K.
Publication year - 2014
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.201310280
Subject(s) - sulfonate , acetylide , chemistry , carbon atom , substrate (aquarium) , catalysis , polymer chemistry , atom (system on chip) , combinatorial chemistry , carbon fibers , leaving group , photochemistry , organic chemistry , materials science , ring (chemistry) , composite number , oceanography , computer science , composite material , embedded system , geology , sodium
Differently substituted terminal alkynes that bear sulfonate leaving groups at an appropriate distance were converted in the presence of a propynyl gold(I) precatalyst. After initial formation of a gold acetylide, a cyclization takes place at the β‐carbon atom of this species. Mechanistic studies support a mechanism that is related to that of dual gold‐catalyzed reactions, but for the new substrates, only one gold atom is needed for substrate activation. After formation of a gold vinylidene complex, which forms a tight contact ion pair with the sulfonate leaving group, recombination of the two parts delivers vinyl sulfonates, which are valuable targets that can serve as precursors for cross‐coupling reactions, for example.