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- Title
Manganese(I)‐Catalyzed Chemoselective Transfer Hydrogenation of the C=C Bond in Conjugated Ketones at Room Temperature.
- Authors
Sharma, Dipesh M.; Shabade, Anand B.; Gonnade, Rajesh G.; Punji, Benudhar
- Abstract
Chemoselective transfer hydrogenation of C=C bond in α,β‐unsaturated ketones is demonstrated at room temperature employing a manganese(I) catalyst and half an equivalent of ammonia‐borane (H3N−BH3). A series of mixed‐donor pincer‐ligated Mn(II) complexes, (tBu2PN3NPyz)MnX2 [κP,κN,κN‐(N‐(di‐tert‐butylphosphaneyl)‐6‐(1H‐pyrazol‐1‐yl)pyridin‐2‐amine)MnX2] {X=Cl (Mn2), X=Br (Mn3), X=I (Mn4)} were synthesized and characterized. Amongst the Mn(II) complexes, (Mn2, Mn3, Mn4) and Mn(I) complex, (tBu2PN3NPyz)Mn(CO)2Br (Mn1) screened; the Mn1 acts as an efficient catalyst for the chemoselective C=C bond reduction in α,β‐unsaturated ketones. Various synthetically important functionalities like halides, methoxy, trifluoromethyl, benzyloxy, nitro, amine, and unconjugated alkene and alkyne groups, including heteroarenes, were compatible and provided saturated ketones in excellent yields (up to 97 %). A preliminary mechanistic study highlighted the crucial role of metal–ligand (M–L) cooperation through the dearomatization‐aromatization process in catalyst Mn1 for the chemoselective C=C bond transfer hydrogenation.
- Subjects
TRANSFER hydrogenation; KETONES; MANGANESE; ALKENES; HETEROARENES; TEMPERATURE; NITROALKENES
- Publication
Chemistry - A European Journal, 2023, Vol 29, Issue 43, p1
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.202301174