Copper(I)-Catalyzed Tandem Carboarylation/Cyclization of Alkynyl Phosphonates with Diaryliodonium Salts

被引：31

作者：

Perez-Saavedra, Borja ^{[1
]}

Vazquez-Galinanes, Nuria ^{[1
]}

Saa, Carlos ^{[1
]}

Fananas-Mastral, Martin ^{[1
]}

机构：

[1] Univ Santiago de Compostela, Dept Quim Organ, Ctr Singular Invest Quim Biolox & Mat Mol CIQUS, Santiago De Compostela 15782, Spain

来源：

ACS CATALYSIS | 2017年 / 7卷 / 09期

关键词：

copper; diaryliodonium salts; phosphonates; alkynes; carbocations; COPPER-CATALYZED CARBOARYLATION; HALO-ENOL PHOSTONES; VINYLIC CATIONS; ACID MONOESTERS; RING-CLOSURE; ARYLATION; PHOSPHAISOCOUMARINS; HALOCYCLIZATION; REARRANGEMENT; CYCLIZATION;

D O I：

10.1021/acscatal.7b02434

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

A copper-catalyzed tandem carboarylation/cyclization of alkynyl phosphonates with diaryliodonium salts is reported. The reaction gives straightforward access to valuable cyclic enol phosphonates in good yields under mild conditions. This transformation entails an initial chemoselective arylation of the alkyne followed by an intramolecular trapping of an intermediate vinyl cation by the phosphoryl group. Observation of beta-aryl rearrangements across the double bond in intermediates generated from 1,2-diaryl alkynes support the intermediacy of a vinyl cation.

引用

页码：6104 / 6109

页数：6

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