Deterium-labeled (hetero)aryl bromide
is one of the most widespread
applicable motifs to achieve important deuterated architectures for
various scientific applications. Traditionally, these deterium-labeled
(hetero)aryl bromides are commonly prepared via multistep syntheses.
Herein, we disclose a direct H/D exchange protocol for deuteration
of (hetero)aryl bromides using Ag2CO3 as catalyst
and D2O as deuterium source. This protocol is highly efficient,
simply manipulated, and appliable for deuterium-labeling of over 55
(hetero)aryl bromides including bioactive druglike molecules and key
intermediates of functional materials. In addition, this method showed
distinguishing site-selectivity toward the existing transition-metal-catalyzed
HIE process, leading to multideuterated (hetero)aryl bromides in one
step.
Ag2CO3-catalyzed hydrogen isotope exchange
of five-membered heteroarenes is disclosed. The reaction can be conducted
in the open air, at ambient temperature, and with D2O as
deuterium source. Moreover, this protocol showed orthogonal site selectivity
to existing technology, thereby greatly expanding the scope of substrates
for HIE reaction. The mechanistic study indicated that the carbonate
group plays a crucial role to achieve high levels of deuterium incorporation
by lowering the activation energy of H/D exchange process.
An efficient approach to install deuterium into mono-fluorinated (hetero)arenes by Ag2CO3/Sphos mediated HIE protocol with D2O as deuterium source has been disclosed. This method showed specific site-selectivity of deuteration at...
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