Gold-Catalyzed C(sp2)-C(sp) Coupling by Alkynylation through Oxidative Addition of Bromoalkynes

被引：41
|
作者：
Yang, Yangyang [1 ]
Schiessl, Jasmin [1 ]
Zallouz, Sirine [1 ]
Goeker, Verena [1 ]
Gross, Juergen [1 ]
Rudolph, Matthias [1 ]
Rominger, Frank [1 ]
Hashmi, A. Stephen K. [1 ,2 ]
机构：
[1] Heidelberg Univ, Organ Chem Inst, Neuenheimer Feld 270, D-69120 Heidelberg, Germany
[2] King Abdulaziz Univ, Chem Dept, Fac Sci, Jeddah 21589, Saudi Arabia
来源：
CHEMISTRY-A EUROPEAN JOURNAL | 2019年 / 25卷 / 41期
关键词：
allenes; cross-coupling; gold catalysis; heterocycles; oxidative addition; INJECTION FIELD DESORPTION/IONIZATION; VISIBLE-LIGHT PHOTOREDOX; PHOTOSENSITIZER-FREE; ORGANOGOLD COMPOUNDS; ACTIVATION; COMPLEXES; REACTIVITY;
D O I：
10.1002/chem.201902213
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A gold(I)-catalyzed cascade cyclization-alkynylation of allenoates using alkynyl bromide to generate beta-alkynyl-gamma-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 beta-alkynyl-gamma-butenolides in moderate to good yields without the need for any external oxidant.
引用
收藏
页码：9624 / 9628
页数：5
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