Journal
NANO RESEARCH
Volume 12, Issue 7, Pages 1659-1662Publisher
TSINGHUA UNIV PRESS
DOI: 10.1007/s12274-019-2416-6
Keywords
hydrogenation; chemoselectivity; enantioselectivity; PtAu; bimetallic
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Funding
- National Key R&D Program of China [2017YFA0505200]
- National Natural Science Foundation of China [21625104, 21521091]
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Herein, we present a new strategy that for the first time achieved chemo- and enantio-selective hydrogenation of alkenes over arylhalides. Key to the success is that instead of using external poisons, we use the composition of the bimetallic nanocrystal catalysts to control chemoselectivity (hydrogenation of C=C bonds without cleavage of Ar-X bonds). We further show that this system combined with surface modifying chiral ligands can control the enantioselectivity. Thus, after synthesizing and screening a series of easily accessible MxAuy (M = Pd, Pt; x, y = 1, 3, 5) bimetallic nanocrystals (9-10 nm) supported on activated carbon, we identified that Pt1Au1/C is a recyclable and generally applicable catalyst for the chemoselective hydrogenation of alkenes without cleaving aryl halogen bonds. Furthermore, cinchonidine modified Pt1Au1/C is shown to be capable of enantioselective hydrogenation, as illustrated by the rapid and enantio-enriched synthesis of RIP1 inhibitor analogue 7-Br-O-Nec1.
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