On the Gold-Catalyzed Generation of Vinyl Cations from 1,5-Diynes

被引：85

作者：

Wurm, Thomas ^{[1
]}

Bucher, Janina ^{[1
]}

Duckworth, Sarah B. ^{[1
]}

Rudolph, Matthias ^{[1
]}

Rominger, Frank ^{[1
]}

Hashmi, A. Stephen K. ^{[1
,2
]}

机构：

[1] Heidelberg Univ, Organisch Chem Inst, Neuenheimer Feld 270, D-69120 Heidelberg, Germany

[2] King Abdulaziz Univ, Fac Sci, Dept Chem, Jeddah 21589, Saudi Arabia

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2017年 / 56卷 / 12期

关键词：

extended pi-systems; gold catalysis; high-energy intermediates; pentalenes; vinyl cations; GOLD(I)-CATALYZED CYCLOISOMERIZATION; DIYNES; CYCLIZATION; COMPLEXES; DERIVATIVES; ACTIVATION; 1,6-DIYNES; ACCESS; SELECTIVITY; ACETYLIDES;

D O I：

10.1002/anie.201700057

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Conjugated 1,5-diynes bearing two aromatic units at the alkyne termini were converted in the presence of a gold catalyst. Under mild conditions, aryl-substituted dibenzopentalenes were generated. Calculations predict that aurated vinyl cations are key intermediates of the reaction. A bidirectional approach provided selective access to the angular annulated product in high yield, which was explained by calculations.

引用

页码：3364 / 3368

页数：5

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