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DOI: 10.1055/s-0042-1753402
Pd/C Catalyzed Dehalogenation of (Hetero)aryls Using Triethylsilane as Hydrogen Donor


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.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0042-1753402.
- Supporting Information
Publication History
Received: 09 November 2022
Accepted after revision: 23 January 2023
Article published online:
27 February 2023
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