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Gold‐Catalyzed C(sp 2 )−C(sp) Coupling by Alkynylation through Oxidative Addition of Bromoalkynes
Author(s) -
Yang Yangyang,
Schießl Jasmin,
Zallouz Sirine,
Göker Verena,
Gross Jürgen,
Rudolph Matthias,
Rominger Frank,
Hashmi A. Stephen K.
Publication year - 2019
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201902213
Subject(s) - alkynylation , catalysis , chemistry , bromide , functional group , coupling reaction , reaction conditions , cascade , coupling (piping) , combinatorial chemistry , medicinal chemistry , organic chemistry , materials science , chromatography , metallurgy , polymer
Abstract A gold(I)‐catalyzed cascade cyclization–alkynylation of allenoates using alkynyl bromide to generate β‐alkynyl‐γ‐butenolides was investigated. Whereas alkynyl iodides afforded significant amounts of the homo‐coupling of two lactone units, alkynyl bromides led to a selective reaction, and a broad functional group tolerance was observed. Under the optimized reaction conditions, it was possible to directly synthesize a large range of β‐alkynyl‐γ‐butenolides in moderate to good yields without the need for any external oxidant.