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
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 reagent...
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| Veröffentlicht in: | Organic process research & development 2020-01, Vol.24 (1), p.106-110 |
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| container_title | Organic process research & development |
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| creator | Hari, Durga Prasad Caramenti, Paola Schouwey, Lionel Chang, Miyeon Nicolai, Stefano Bachert, Donald Wright, Timothy Orella, Chuck Waser, Jerome |
| description | 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. |
| doi_str_mv | 10.1021/acs.oprd.9b00498 |
| format | Article |
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Process Res. Dev</addtitle><date>2020-01-17</date><risdate>2020</risdate><volume>24</volume><issue>1</issue><spage>106</spage><epage>110</epage><pages>106-110</pages><issn>1083-6160</issn><eissn>1520-586X</eissn><abstract>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. 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| source | American Chemical Society Journals |
| title | 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 |
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