Transfer Hydrogenolysis of O‐ and N‐Benzyl Groups in Water with Tetrahydroxydiboron by Using an Amphiphilic Polymer‐Supported Nano‐Palladium Catalyst

Author:

Zhang Kaili12,Okumura Shintaro132,Uozumi Yasuhiro12ORCID

Affiliation:

1. Institute for Molecular Science Myodaiji Okazaki 444-0864 Japan

2. SOKENDAI (Graduate University for Advanced Studies) Myodaiji Okazaki 444-0864 Japan

3. Department of Synthetic Chemistry and Biological Chemistry Kyoto University

Abstract

AbstractDebenzylation of O‐ and N‐benzyl groups was achieved under safe and mild conditions by using B2(OH)4 as an alternative to gaseous hydrogen in the presence of an amphiphilic polystyrene‐poly(ethylene glycol) resin‐supported nano‐palladium catalyst (ARP−Pd) in water. Benzyl groups of a variety of benzylic ethers, esters, carbamates, and amines, including benzyl‐protected carbohydrates and amino acids, were reductively removed in high yields. ARP−Pd was recovered by simple filtration and reused seven times without a significant loss of its catalytic activity.

Publisher

Wiley

Reference58 articles.

1. Greene's Protective Groups in Organic Synthesis

2. Compound summaries of molecular hydrogen: CAS 1333–74-0; PubChem CID 783; GHS class 1; GHS hazzard statement H220 (extremely flammable).

3. Selected recent methods ofO-debenzylation see:

4. Pd-Catalyzed Debenzylation and Deallylation of Ethers and Esters with Sodium Hydride

5. Catalytic Transfer Hydrodebenzylation with Low Palladium Loading

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