Journal
ORGANIC PROCESS RESEARCH & DEVELOPMENT
Volume 24, Issue 1, Pages 106-110Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.oprd.9b00498
Keywords
alkynylation; hypervalent iodine reagents; acetylene; EBX; stability
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Funding
- Swiss National Science Foundation [200021_159920]
- European Research Council (ERC Starting Grant) [334840]
- EPFL
- Swiss National Science Foundation (SNF) [200021_159920] Funding Source: Swiss National Science Foundation (SNF)
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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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