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분자활성 촉매반응 연구단
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The Mechanism of Copper-Catalyzed Trifunctionalization of Terminal Allenes

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Title
The Mechanism of Copper-Catalyzed Trifunctionalization of Terminal Allenes
Author(s)
Hong Ki Kim; Manoj V. Mane; John Montgomery; Mu Hyun Baik
Publication Date
2019-07
Journal
CHEMISTRY-A EUROPEAN JOURNAL, v.25, no.40, pp.9456 - 9463
Publisher
WILEY-V C H VERLAG GMBH
Abstract
A highly selective copper-catalyzed trifunctionalization of allenes has been established based on diborylation/cyanation with bis(pinacolato)diboron (B 2 pin 2 ) and N-cyano-N-phenyl-p-toluenesulfonamide (NCTS). The Cu-catalyzed trifunctionalization of terminal allenes is composed of three catalytic reactions (first borocupration, electrophilic cyanation, and second borocupration) that provide a densely functionalized product with regio-, chemo- and diastereoselectivity. Allene substrates have multiple reaction-sites, and the selectivities are determined by the suitable interactions (e.g., electronic and steric demands) between the catalyst and substrates. We employed DFT calculations to understand the cascade copper-catalyzed trifunctionalization of terminal allenes, providing densely-functionalized organic molecules with outstanding regio-, chemo- and diastereoselectivity in high yields. The selectivity challenges presented by cumulated π-systems are addressed by systematic computational studies; these give insight to the catalytic multiple-functionalization strategies and explain the high selectivities that we see for these reactions. © 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
URI
https://pr.ibs.re.kr/handle/8788114/6295
ISSN
0947-6539
Appears in Collections:
Center for Catalytic Hydrocarbon Functionalizations(분자활성 촉매반응 연구단) > Journal Papers (저널논문)
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