Protecting group
chemistry has invariably captured the fascination
of chemists because of its extensive viability in chemical synthesis.
The present report describes our pioneer work of applying ytterbium
triflate as a catalyst, for the reaction of alcohols with di-
tert
-butyl dicarbonate (Boc
2
O) leading to the
formation of
tert
-butyl ethers. There exists no recorded
evidence for the use of Yb(OTf)
3
as a catalyst for the
protection of alcohols to
tert
-butyl ethers, despite
its excellent utility in various reactions. Yb(OTf)
3
has
been used predominantly in the catalytic deprotection studies such
as selective deprotection of
tert
-butyl esters to
carboxylic acids as well as prenyl ethers to alcohols. This study
involved the critical evaluation of solvent, time, and temperature
that finally led to an efficient protocol for the formation of
tert
-butyl ethers. Yb(OTf)
3
catalyzed the formation
of
tert
-butyl ethers, notably reducing the reaction
time, which is exemplified by the achievement of up to 92% conversion
of alcohols to
tert
-butyl ethers within an hour.
Additionally, the report demonstrates the utility of this synthetic
protocol for the protection of carboxylic acids.
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