Aromatic Azido-selective Reduction via the Staudinger Reaction Using Tri-n-butylphosphonium Tetrafluoroborate with Triethylamine

被引：27

作者：

Meguro, Tomohiro ^{[1
]}

Yoshida, Suguru ^{[1
]}

Hosoya, Takamitsu ^{[1
]}

机构：

[1] Tokyo Med & Dent Univ, Inst Biomat & Bioengn, Lab Chem Biosci, Chiyoda Ku, 2-3-10 Kanda Surugadai, Tokyo 1010062, Japan

来源：

CHEMISTRY LETTERS | 2017年 / 46卷 / 04期

关键词：

Azide; Staudinger reaction; Aniline; FACILE SYNTHESIS; PROBES; CYCLOADDITIONS; ARYNE; ACIDS;

D O I：

10.1246/cl.161159

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An efficient method for the reduction of aromatic azides to anilines via the Staudinger reaction using tri-n-butylphosphonium tetrafluoroborate with triethylamine in aqueous tetrahydrofuran solution is reported. The method enables the aromatic azido-selective reduction of 3-azido-5-(azidomethyl) benzene derivatives to efficiently afford anilines bearing an azidomethyl group.

引用

页码：473 / 476

页数：4

共 33 条

[1] A reduction-triggered fluorescence probe for sensing nucleic acids [J].

Abe, Hiroshi ;

Wang, Jin ;

Furukawa, Kazuhiro ;

Oki, Kazuma ;

Uda, Miwako ;

Tsuneda, Satoshi ;

Ito, Yoshihiro .

BIOCONJUGATE CHEMISTRY, 2008, 19 (06) :1219-1226

[2]

Aitken R. A., 2004, ORGANOPHOSPHORUS REA, P87

[3]

Deeb A., 2013, EUR CHEM B, V2, P981

[4] RECENT ADVANCES IN THE STAUDINGER REACTION [J].

GOLOLOBOV, YG ;

KASUKHIN, LF .

TETRAHEDRON, 1992, 48 (08) :1353-1406

[5] 60 YEARS OF STAUDINGER REACTION [J].

GOLOLOBOV, YG ;

ZHMUROVA, IN ;

KASUKHIN, LF .

TETRAHEDRON, 1981, 37 (03) :437-472

[6] 3-Azidodifluoromethyl-3H-diazirin-3-yl group as an all-in-one functional group for radioisotope-free photoafiinity labeling [J].

Hiramatsu, Toshiyuki ;

Guo, Ying ;

Hosoya, Takamitsu .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2007, 5 (18) :2916-2919

[7] Design of dantrolene-derived probes for radioisotope-free photoaffinity labeling of proteins involved in the physiological Ca2+ release from sarcoplasmic reticulum of skeletal muscle [J].

Hosoya, T ;

Hiramatsu, T ;

Ikemoto, T ;

Aoyama, H ;

Ohmae, T ;

Endo, M ;

Suzuki, M .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2005, 15 (05) :1289-1294

[8] Novel bifunctional probe for radioisotope-free photoaffinity labeling: compact structure comprised of photospecific ligand ligation and detectable tag anchoring units [J].

Hosoya, T ;

Hiramatsu, T ;

Ikemoto, T ;

Nakanishi, M ;

Aoyama, H ;

Hosoya, A ;

Iwata, T ;

Maruyama, K ;

Endo, M ;

Suzuki, M .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2004, 2 (05) :637-641

[9] Facile synthesis of diazido-functionalized biaryl compounds as radioisotope-free photoaffinity probes by Suzuki-Miyaura coupling [J].

Hosoya, Takamitsu ;

Inoue, Atsushi ;

Hiramatsu, Toshiyuki ;

Aoyama, Hiroshi ;

Ikemoto, Takaaki ;

Suzuki, Masaaki .

BIOORGANIC & MEDICINAL CHEMISTRY, 2009, 17 (06) :2490-2496

[10] Functional Role of Neuroendocrine-Specific Protein-Like 1 in Membrane Translocation of GLUT4 [J].

Ikemoto, Takaaki ;

Hosoya, Takamitsu ;

Takata, Kumi ;

Aoyama, Hiroshi ;

Hiramatsu, Toshiyuki ;

Onoe, Hirotaka ;

Suzuki, Masaaki ;

Endo, Makoto .

DIABETES, 2009, 58 (12) :2802-2812

← 1 2 3 4 →