Affiliation:
1. Department of Chemical Science and Engineering Kobe University 1-1 Rokkodai, Nada Kobe 657-8501 Japan
2. Research Center for Membrane and Film Technology Kobe University 1-1 Rokkodai, Nada Kobe 657-8501 Japan
Abstract
AbstractLochmann–Schlosser base, a stoichiometric combination of nBuLi and KOtBu, is commonly used as a superbase for deprotonating a wide range of organic compounds. In the present study, we report that catalytic potassium hexamethyldisilazide (KHMDS) exhibits higher catalytic activity than KOtBu for successive bromine–metal exchanges. Accordingly, 1–10 mol% of KHMDS dramatically enhances halogen dance reactions to introduce various electrophiles to bromopyridine, bromoimidazole, bromothiophene, bromofuran, and bromobenzene derivatives with the bromo group translocated from the original position. A dual catalytic cycle is proposed to explain the ultrafast bromine transfer.
Cited by
3 articles.
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