Gold‐Catalyzed C(sp 2 )−C(sp) Coupling by Alkynylation through Oxidative Addition of Bromoalkynes | Zendy

Yang Yangyang | Zendy; Schießl Jasmin | Zendy; Zallouz Sirine | Zendy; Göker Verena | Zendy; Gross Jürgen | Zendy; Rudolph Matthias | Zendy; Rominger Frank | Zendy; Hashmi A. Stephen K. | Zendy

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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

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.

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