Synlett 2017; 28(05): 560-564
DOI: 10.1055/s-0036-1588915
letter
© Georg Thieme Verlag Stuttgart · New York

Synthesis and Photochemistry of a New Photolabile Protecting Group for Propargylic Alcohols

Chi Ma
a  School of Chemistry and Chemical Engineering, Tianjin University of Technology, Tianjin 300384, P. R. of China   eMail: zhanghuan80887@163.com   eMail: youlaimail@163.com
,
Youlai Zhang*
a  School of Chemistry and Chemical Engineering, Tianjin University of Technology, Tianjin 300384, P. R. of China   eMail: zhanghuan80887@163.com   eMail: youlaimail@163.com
,
Huan Zhang*
a  School of Chemistry and Chemical Engineering, Tianjin University of Technology, Tianjin 300384, P. R. of China   eMail: zhanghuan80887@163.com   eMail: youlaimail@163.com
,
Junru Li
a  School of Chemistry and Chemical Engineering, Tianjin University of Technology, Tianjin 300384, P. R. of China   eMail: zhanghuan80887@163.com   eMail: youlaimail@163.com
,
Yasuhiro Nishiyama
b  Graduate School of Materials Science, Nara Institute of Science and Technology (NAIST), 8916-5 Takayama, Ikoma, Nara 630-0192, Japan
,
Hiroki Tanimoto
b  Graduate School of Materials Science, Nara Institute of Science and Technology (NAIST), 8916-5 Takayama, Ikoma, Nara 630-0192, Japan
,
Tsumoru Morimoto
b  Graduate School of Materials Science, Nara Institute of Science and Technology (NAIST), 8916-5 Takayama, Ikoma, Nara 630-0192, Japan
,
Kiyomi Kakiuchi
b  Graduate School of Materials Science, Nara Institute of Science and Technology (NAIST), 8916-5 Takayama, Ikoma, Nara 630-0192, Japan
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Publikationsverlauf

Received: 03. September 2016

Accepted after revision: 21. Oktober 2016

Publikationsdatum:
15. November 2016 (eFirst)

Abstract

A new and efficient thiochromenone S,S-dioxide-based photolabile protecting group for propargylic alcohols is described. Robust protection reactions were developed through copper (II)-catalyzed substitution of propargylic alcohols. Subsequent photodeprotection proceeded smoothly to give the corresponding propargylic alcohols quantitatively within 15 minutes, as demonstrated by 1H NMR spectroscopy and HPLC. Notably, the photoproduct derived from the thiochromenone derivatives showed a high fluorescence quantum yield, permitting monitoring of the reaction progress by fluorescence spectroscopy. A new strategy for the synthesis of triazoles by a one-pot reaction is also presented.

Supporting Information

 
  • References and Notes

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