1. Pd/C Catalyzed Dehalogenation of (Hetero)aryls Using Triethyl-silane as Hydrogen Donor.
- Author
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La Torre, Mathéo, Maton, William, Cleator, Ed, and Jouffroy, Matthieu
- Subjects
DEHALOGENATION ,HYDROGEN content of metals ,HYDROGEN ,FUNCTIONAL groups ,PALLADIUM ,DEBROMINATION - Abstract
(Hetero)aryl dehalogenation is a classical transformation usually performed using hydrogen gas and a metal supported on carbon, notably palladium (Pd/C). Though efficient, the need for a milder and operationally simple dehalogenation can arise. We found that the combination of Pd/C as catalyst and triethylsilane (TES) as hydrogen donor in THF resulted in a broadly applicable, easy to set up, and scalable debromination and deiodination. Optimization of the reaction showed that 1 mol% of Pd/C and 4 equiv of TES at room temperature were sufficient to obtain full conversion of most synthons of pharmaceutical interest in 4–24 h. The newly found conditions were applied to a large range of aromatic and heteroaromatic substrates, affording the desired targets in good to excellent yields with an exceptional functional group tolerance. [ABSTRACT FROM AUTHOR]
- Published
- 2023
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