Reduction of phenylacetylenes using Raney Ni-Al alloy, Al powder in the presence of noble metal catalysts in water

Rayhan, Ummey; Kowser, Zannatul; Islam, Md. Nurul; Redshaw, Carl; Yamato, Takehiko

Abstract

Dedicated to Prof. Kenneth Laali on the occasion of his 66th birthday Received mm-dd-yyyy Accepted mm-dd-yyyy Published on line mm-dd-yyyy Dates to be inserted by editorial office Abstract The chemoselective reduction is based on the reaction of Raney Ni–Al alloy with Al powder in water which produces in situ hydrogen to utilize the hydrogenation of the targeted functional groups. Raney Ni–Al alloy with Al powder can reduce phenylacetylenes to the corresponding ethylbenzene (3) in water in excellent yield at 120 °C for 6 h in a sealed tube. In addition, the complete reduction of aromatic ring to ethylcyclohexane (4) required 60 °C for 12 h with Raney Ni–Al alloy, Al powder in the presence of Pt/C. The appropriate selection of the reaction conditions allowed the selective preparation of ethylbenzene as well as ethylcyclohexane from phenylacetylene. 1a : R = H ,1b : R = CH 3 , 1c : R = OCH 3 ,1d : R = C(CH 3) 3

Citation

Rayhan, U., Kowser, Z., Islam, M. N., Redshaw, C., & Yamato, T. (2017). Reduction of phenylacetylenes using Raney Ni-Al alloy, Al powder in the presence of noble metal catalysts in water. Arkivoc, 2018(2), 241-251. https://doi.org/10.24820/ark.5550190.p010.277

• Journal Article Type: Article
• Acceptance Date: Nov 29, 2017
• Online Publication Date: Dec 13, 2017
• Publication Date: Dec 13, 2017
• Deposit Date: Mar 4, 2018
• Publicly Available Date: Mar 5, 2018
• Print ISSN: 1551-7012
• Publisher: Michigan Publishing
• Peer Reviewed: Peer Reviewed
• Volume: 2018
• Issue: 2
• Pages: 241-251
• DOI: https://doi.org/10.24820/ark.5550190.p010.277
• Keywords: Reduction; Phenylacetylene; Raney Ni-Al alloy; Noble metal catalyst; Al powder; Water; Cyclohexane ring
• Public URL: https://hull-repository.worktribe.com/output/710154
• Publisher URL: http://www.arkat-usa.org/get-file/61938/
• Contract Date: Mar 5, 2018