Modular synthesis of bis- and tris-1,2,3-triazoles by permutable sequential azide-aryne and azide-alkyne cycloadditions

被引：51

作者：

Yoshida, Suguru ^{[1
]}

Nonaka, Takako ^{[1
]}

Morita, Takamoto ^{[1
]}

Hosoya, Takamitsu ^{[1
]}

机构：

[1] Tokyo Med & Dent Univ, Inst Biomat & Bioengn, Lab Chem Biosci, Chiyoda Ku, Tokyo 1010062, Japan

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2014年 / 12卷 / 38期

关键词：

CLICK CHEMISTRY; CARBON-CARBON; GENERATION; BENZYNES; 1,2,3-TRIAZOLES; CONSTRUCTION; DERIVATIVES; INSERTION; LIGATION; TRIFLATE;

D O I：

10.1039/c4ob01654h

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A modular synthetic method for bis- and tris-1,2,3-triazoles that include a benzotriazole structure was developed on the basis of sequential azide-aryne and azide-alkyne cycloadditions. The key to success was efficient halogen-metal exchange reaction-mediated generation of aryne from ortho-iodoaryl triflates bearing a base-sensitive terminal alkyne moiety, which was achieved using trimethylsilylmethyl Grignard reagent.

引用

页码：7489 / 7493

页数：5

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