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[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst
Published on: May 21, 2019
Copper-loaded nanocellulose sponge as a sustainable catalyst for regioselective hydroboration of alkynes
Congcong Zhang1, Mi Zhou2, Shiwen Liu2
1Key Lab of Science and Technology of Eco-Textile, Ministry of Education, College of Chemistry, Chemical Engineering and Biotechnology, Donghua University, Shanghai 201620, China.
Abstract:
It is desirable for catalyst supports to be biodegradable, easily-modifiable, and possessing high surface area. In this work, thiolated nanocellulose sponge was prepared from hydrolytic silane condensation of cellulose nanofibrils (CNF) and used as a green support to immobilize copper cations via in situ CuII to CuI reduction and complexation. The sponge featured high porosity (90.5%) and low density (29.4 mg/cm3) with regular morphology. The sponge easily recovered 94% of its original shape in water after experiencing 80% deformation under stress of 95 kPa. When used in catalyzing hydroboration of alkynes, excellent conversion and up to 99% regioselectivity were achieved with the copper-loaded sponge. The sponge-supported catalysts worked well in the absence of additional ligands, had a broad substrate scope, and retained 93% of their activity after six catalytic cycles. This simple and scalable strategy offers an efficient route for immobilizing metal catalysts on porous supports.
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One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
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