Phosphazene-Base-CatalyzedTandem Addition-Cyclization Reaction of o-Alkynylbenzaldehydewith Oxygen and Nitrogen Nucleophiles

Phosphazene-Base-CatalyzedTandem Addition-Cyclization Reaction of o-Alkynylbenzaldehydewith Oxygen and Nitrogen Nucleophiles
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磷腈碱催化邻炔基苯甲醛与氧、氮亲核试剂的串联加成环化反应

DOI:
10.1055/s-0028-1087909
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发表时间:
2009
期刊:
影响因子:
--
通讯作者:
M. Terada
M. Terada
中科院分区:
--
文献类型:
--
作者:
C. Kanazawa;A. Ito;M. Terada

文献摘要

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研究了磷腈碱P4-tBu催化邻炔基苯甲醛与亲核试剂的串联加成环合反应。亲核环化反应不仅由醇类(包括空间要求高的醇类)有效地引发,而且在催化量的P4-tBu的影响下由氮亲核试剂(如酰胺和吡咯)有效地引发。该方法能够在温和的条件下有效地获得异苯并呋喃衍生物。
The tandem addition-cyclization reaction between o-alkynylbenzaldehyde and nucleophile catalyzed by P4- t Bu, a phosphazene base, is demonstrated. The nucleophilic cyclization is efficiently triggered not only by alcohols, including sterically demanding ones, but also by nitrogen nucleophiles, such as amide and pyrrole, under the influence of a catalytic amount of P4- t Bu. The method enables efficient access to isobenzofuran derivatives under mild conditions.