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분자활성 촉매반응 연구단
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How bulky ligands control the chemoselectivity of Pd-catalyzed: N -arylation of ammonia

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Title
How bulky ligands control the chemoselectivity of Pd-catalyzed: N -arylation of ammonia
Author(s)
Seoung-Tae Kim; Suyeon Kim; Mu-Hyun Baik
Publication Date
2020-01
Journal
CHEMICAL SCIENCE, v.11, no.4, pp.1017 - 1025
Publisher
ROYAL SOC CHEMISTRY
Abstract
This journal is © The Royal Society of Chemistry.Steric bulk has been recognized as a central design principle for supporting ligands in the widely utilized Buchwald-Hartwig amination. In a recent example, it was shown that a Pd-catalyst carrying a phosphine ligand can successfully aminate aryl halides using ammonia as the nitrogen source. Interestingly, the chemoselectivity of this reaction was found to depend on the steric demand of the phosphine ligand. Whereas a sterically less demanding phosphine affords diphenylamine as the major product, it was shown that the amination reaction can be stopped after the first amination to give aniline if a sterically more encumbering phosphine ligand is used. Density functional theory calculations were carried out to examine the relationship between the steric demand of the phosphine ligand and the chemoselectivity. It was found that the key feature that leads to the chemoselectivity is the ability of the phosphine ligand to rotate the biaryl moiety of the ligand away from the Pd-center upon amine addition to release some of the steric crowding from the Pd-coordination site
URI
https://pr.ibs.re.kr/handle/8788114/7028
ISSN
2041-6520
Appears in Collections:
Center for Catalytic Hydrocarbon Functionalizations(분자활성 촉매반응 연구단) > Journal Papers (저널논문)
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