Straightforward Synthesis of Indenes by Gold-Catalyzed Intramolecular Hydroalkylation of Ynamides

被引：5

作者：

Thilmany, Pierre ^{[1
]}

Guarnieri-Ibanez, Alejandro ^{[2
]}

Jacob, Clement ^{[1
,3
]}

Lacour, Jerome ^{[2
]}

Evano, Gwilherm ^{[1
]}

机构：

[1] Univ libre Bruxelles ULB, Serv Chim & Phys Chim Organ, Lab Chim Organ, B-1050 Brussels, Belgium

[2] Univ Geneva, Dept Organ Chem, CH-1211 Geneva 4, Switzerland

[3] Univ Antwerp, Dept Chem, Organ Synth Div, B-2020 Antwerp, Belgium

来源：

ACS ORGANIC & INORGANIC AU | 2022年 / 2卷 / 01期

基金：

瑞士国家科学基金会;

关键词：

gold catalysis; ynamides; indenes; H-shift; hydroalkylation; NITROGEN NUCLEOPHILES. PREPARATION; KETENIMINIUM IONS; TERMINAL ALKYNES; CYCLIZATION; REACTIVITY; 1,1-DIBROMO-1-ALKENES; EFFICIENT; REAGENTS; ALKYNYLATION; COMPLEXES;

D O I：

10.1021/acsorginorgau.1c00021

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An original and straightforward entry to polysubstituted indenes from readily available ynamides is reported. Upon reaction with a N-heterocyclic carbene-gold complex under mild conditions, activated keteniminium ions are generated whose unique electrophilicity triggers a [1,5]-hydride shift and a subsequent cyclization. The presence of an endocyclic enamide in the densely functionalized resulting indenes was shown to be especially useful and versatile, offering a range of opportunities for their further postfunctionalization.

引用

页码：53 / 58

页数：6

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