β‑Amino Phosphine Mn Catalysts for 1,4-Transfer Hydrogenation of Chalcones and Allylic Alcohol Isomerization

Mn complexes with amino acid derived PN ligands were used in the catalytic transfer hydrogenation (TH) of ketone and chalcone substrates in 2-propanol with mild heating. Moreover, chalcones are reduced selectively to the saturated ketone at short times and can be fully converted to the alcohol when...

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Bibliographic Details
Published in:Organometallics 2019-11, Vol.38 (22), p.4387-4391
Main Authors: Vigneswaran, Vipulan, MacMillan, Samantha N, Lacy, David C
Format: Article
Language:English
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Summary:Mn complexes with amino acid derived PN ligands were used in the catalytic transfer hydrogenation (TH) of ketone and chalcone substrates in 2-propanol with mild heating. Moreover, chalcones are reduced selectively to the saturated ketone at short times and can be fully converted to the alcohol when reactions are prolonged. The mechanism of chalcone reduction was briefly considered. Allylic alcohols are not reactive in 2-propanol, but quantitative isomerization occurs in toluene. Thus, we suspect that the allylic alcohols are dehydrogenated and the resulting ketone is formed through a direct 1,4-hydrogenation of the chalcone. Finally, several other related ligands that have been used in Mn-based TH reactions were explored to test the viability of ligand design in favoring chemoselectivity. The β-amino phosphine ligands proved most effective in this regard.
ISSN:0276-7333
1520-6041
DOI:10.1021/acs.organomet.9b00692