Affiliation:
1. Organic Chemistry Division CSIR – National Chemical Laboratory (CSIR–NCL) Dr. Homi Bhabha Road Pune 411 008 India
2. Academy of Scientific and Innovative Research (AcSIR) Ghaziabad 201002 India
3. Centre for Material Characterization CSIR – National Chemical Laboratory (CSIR–NCL) Dr. Homi Bhabha Road Pune India
Abstract
AbstractChemoselective 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.
Funder
Science and Engineering Research Board
Subject
General Chemistry,Catalysis,Organic Chemistry
Cited by
1 articles.
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