Bifunctional Phosphine Ligand-Enabled Gold(I)-Catalyzed O-Nucleophilic Addition of N-Hydroxybenzo[1,2,3]-triazin-4(3H)-ones to Alkynes Followed by [3,3]-Rearrangement: Simultaneous Formation of C-O and C-N Bonds

被引：5

作者：

Xu, Yongcai ^{[1
]}

Zheng, Kanghe ^{[1
]}

Zhou, Bingwei ^{[1
]}

Jin, Hongwei ^{[1
]}

Liu, Yunkui ^{[1
]}

机构：

[1] Zhejiang Univ Technol, Coll Chem Engn, State Key Lab Breeding Base Green Chem Synth Tech, Hangzhou 310014, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2020年 / 85卷 / 10期

关键词：

CATALYZED DENITROGENATIVE ANNULATION; GOLD(III)-CATALYZED TANDEM REACTION; HIGHLY SELECTIVE SYNTHESIS; REARRANGEMENT; EFFICIENT; CYCLIZATION; 1,2,3-BENZOTRIAZIN-4(3H)-ONES; DERIVATIVES; ACID;

D O I：

10.1021/acs.joc.0c00471

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We describe a gold (I)-catalyzed tandem O-nucleophilic addition/[3,3]-rearrangement reaction of N-hydroxybenzo[1,2,3]-triazin-4(3H)-ones with alkynes enabled by a biphenyl-2-yl phosphine ligand featuring a pendant amide moiety (L1). A variety of 1-(2-oxo-2-arylethyl)benzo [d][1,2,3]triazin-4(1H)-one derivatives were synthesized in good to excellent yields. The present protocol gives a rare example of simultaneous formation of C-O and C-N bonds in the gold(I)-catalyzed [3,3]-sigmatropic rearrangements.

引用

页码：6519 / 6527

页数：9

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