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Ligand-Free (Z)-Selective Transfer Semihydrogenation of Alkynes Catalyzed by in situ Generated Oxidizable Copper Nanoparticles

preprint
submitted on 25.01.2021, 01:10 and posted on 27.01.2021, 10:04 by Rafał Kusy, Karol Grela
Herein, we present (Z)-selective transfer semihydrogenation of alkynes based on in situ generated CuNPs in the presence of hydrogen donors, such as ammonia-borane and a protic solvent. This environmentally-friendly method is characterized by operational simplicity combined with high stereo- and chemoselectivity and functional group compatibility. Auto-oxidation of CuNPs after the semihydrogenation reaction is completed results in the formation of water-soluble ammonia complex, so that the catalyst may be reused several times by simple phase-separation with no need of any special regeneration process. Formed NH4B(OR)4 can be easily transformed back to ammonia-borane or to boric acid. In addition, one-pot tandem sequence involving Suzuki reaction followed by semihydrogenation was presented.

Funding

UMO-2017/25/B/ST5/01274

History

Email Address of Submitting Author

raphal.qs@gmail.com

Institution

Institute of Organic Chemistry Polish Academy of Sciences

Country

Poland

ORCID For Submitting Author

0000-0003-2700-6130

Declaration of Conflict of Interest

No conflict of interest.

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