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  4. One-Pot Synthesis of 1-[(Triisopropylsilyl)ethynyl]-1,2-benziodoxol-3(1H)-one (TIPS-EBX): Process Safety Assessment and Impact of Impurities on Product Stability
 
research article

One-Pot Synthesis of 1-[(Triisopropylsilyl)ethynyl]-1,2-benziodoxol-3(1H)-one (TIPS-EBX): Process Safety Assessment and Impact of Impurities on Product Stability

Hari, Durga Prasad  
•
Caramenti, Paola  
•
Schouwey, Lionel  
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December 24, 2019
Organic Process Research & Development

The hypervalent iodine reagent 1-[(TriIsoPropylSilyl)Ethynyl]-1,2-BenziodoXol-3(1H)-one (TIPS-EBX) is among the most useful electrophilic and somophilic alkynylation reagents. Herein, we report a new synthetic protocol to access this reagent in one step from standard commercially available reagents. Thermal analysis of the synthesis procedure showed only weak exotherms. The compound could be obtained with high purity and stability using this new protocol, but care had to be taken to remove tosylate salts impurities, as they led to a lower thermal stability. TIPS-EBX synthesized using the new procedure displayed no shock sensitivity.

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Type
research article
DOI
10.1021/acs.oprd.9b00498
Web of Science ID

WOS:000508471100012

Author(s)
Hari, Durga Prasad  
Caramenti, Paola  
Schouwey, Lionel  
Chang, Miyeon
Nicolai, Stefano  
Bachert, Donald
Wright, Timothy
Orella, Chuck
Waser, Jerome  
Date Issued

2019-12-24

Published in
Organic Process Research & Development
Volume

24

Issue

1

Start page

106

End page

110

Subjects

Chemistry, Applied

•

Chemistry, Organic

•

Chemistry

•

alkynylation

•

hypervalent iodine reagents

•

acetylene

•

ebx

•

stability

•

hypervalent iodine reagents

•

c-h alkynylation

•

decarboxylative alkynylation

•

chemoselective alkynylation

•

carboxylic-acids

•

alkenes

•

arenes

Editorial or Peer reviewed

REVIEWED

Written at

EPFL

EPFL units
LCSO  
Available on Infoscience
March 3, 2020
Use this identifier to reference this record
https://infoscience.epfl.ch/handle/20.500.14299/166707
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