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1.1.2.4.2 Selective Reduction of Alkenes with Isopropanol Using Nickel Nanoparticles

DOI: 10.1055/sos-SD-226-00024

Hudson, R.; Moores, A.Science of Synthesis: Catalytic Reduction in Organic Synthesis, (2017186.

Alonso, Yus, and co-workers used unsupported nickel nanoparticles produced in situ by reduction with lithium.[‌50‌] The resulting nickel nanoparticles were characterized by transmission electron microscopy and had a diameter of 1.75 ± 1.00 nm. These nanoparticles are active for carbonyl reduction,[‌50‌] and also for alkene reduction (Scheme 20).[‌51‌] The mild and selective reduction of 22 substrates 37 delivered the corresponding hydrogenated products 38 using isopropanol as hydrogen donor in a mixture of isopropanol and tetrahydrofuran at 76 °C. Isopropanol is a very popular hydrogen donor because of its nontoxicity, low cost, and stability. Under these conditions, the catalyst loading was 20 mol%. The final example shown in Scheme 20 is relevant as it leads to the natural product brittonin A [38, R1 = R3 = 3,4,5-(MeO)3C6H2; R2 = H] in excellent yield.

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