While the use of triphenylphosphine
as a reductant is common in
organic synthesis, the resulting triphenylphosphine oxide (TPPO) waste
can be difficult to separate from the reaction product. While a number
of strategies to precipitate TPPO are available, none have been reported
to work in more polar solvents. We report here that mixing ZnCl2 with TPPO precipitates a TPPO–Zn complex in high yield
in several common polar organic solvents. The solvent compatibility
of this procedure and the reliability of the precipitation in the
presence of polar functional groups were examined to show the utility
and limitations of this method.
Prevalence of alkyl alkyl ketones in natural products, their use in biological probes, and their versatility as intermediates in organic synthesis, a wide variety of methods have been developed to access them. The most commonly used methods are the addition of a reactive organometallic reagent to an aldehyde followed by oxidation and the addition of pre‐formed organometallic nucleophiles to carboxylic acid derivatives. While both of these protocols are effective, the organometallic reagents can be limiting with complex, functionalized molecules. This article discusses nickel‐ catalyzed synthesis of ketones from alkyl halides and acid chlorides.
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