Stable Palladium Hydride Catalyzed Intermolecular Hydroamination of Vinylarenes

On Yu Kang; Bo Eun Kim; Seong Jun Park; Do Hyun Ryu; Hwan Jung Lim

doi:10.1002/ajoc.201700636

Stable Palladium Hydride Catalyzed Intermolecular Hydroamination of Vinylarenes

On Yu Kang
, Bo Eun Kim
, Seong Jun Park
, Do Hyun Ryu
, Hwan Jung Lim

Department of Chemistry

Korea Research Institute of Chemical Technology
Sungkyunkwan University
University of Science and Technology UST

Research output: Contribution to journal › Article › peer-review

9 Scopus citations

Abstract

A stable palladium hydride catalyzed intermolecular hydroamination reaction for vinylarenes has been developed. The metal hydride catalyst was prepared by treating PdLCl₂ (L=ligand) with AgOTf (OTf=trifluoromethanesulfonate) and (EtO)₂MeSiH as the hydride source. The optimized reaction conditions were employed for the hydroamination of various styrenes with anilines, sulfonamides, and indoles. Chiral ligands such as 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (BINAP) gave enantioenriched products in good to excellent yields.

Original language	English
Pages (from-to)	451-457
Number of pages	7
Journal	Asian Journal of Organic Chemistry
Volume	7
Issue number	2
DOIs	https://doi.org/10.1002/ajoc.201700636
State	Published - 1 Feb 2018

Keywords

C−N bond formation
enantioselectivity
hydrides
hydroamination
palladium

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10.1002/ajoc.201700636

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title = "Stable Palladium Hydride Catalyzed Intermolecular Hydroamination of Vinylarenes",

abstract = "A stable palladium hydride catalyzed intermolecular hydroamination reaction for vinylarenes has been developed. The metal hydride catalyst was prepared by treating PdLCl2 (L=ligand) with AgOTf (OTf=trifluoromethanesulfonate) and (EtO)2MeSiH as the hydride source. The optimized reaction conditions were employed for the hydroamination of various styrenes with anilines, sulfonamides, and indoles. Chiral ligands such as 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (BINAP) gave enantioenriched products in good to excellent yields.",

keywords = "C−N bond formation, enantioselectivity, hydrides, hydroamination, palladium",

author = "Kang, \{On Yu\} and Kim, \{Bo Eun\} and Park, \{Seong Jun\} and Ryu, \{Do Hyun\} and Lim, \{Hwan Jung\}",

note = "Publisher Copyright: {\textcopyright} 2018 Wiley-VCH Verlag GmbH \& Co. KGaA, Weinheim",

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doi = "10.1002/ajoc.201700636",

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journal = "Asian Journal of Organic Chemistry",

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T1 - Stable Palladium Hydride Catalyzed Intermolecular Hydroamination of Vinylarenes

AU - Kang, On Yu

AU - Kim, Bo Eun

AU - Park, Seong Jun

AU - Ryu, Do Hyun

AU - Lim, Hwan Jung

PY - 2018/2/1

Y1 - 2018/2/1

N2 - A stable palladium hydride catalyzed intermolecular hydroamination reaction for vinylarenes has been developed. The metal hydride catalyst was prepared by treating PdLCl2 (L=ligand) with AgOTf (OTf=trifluoromethanesulfonate) and (EtO)2MeSiH as the hydride source. The optimized reaction conditions were employed for the hydroamination of various styrenes with anilines, sulfonamides, and indoles. Chiral ligands such as 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (BINAP) gave enantioenriched products in good to excellent yields.

AB - A stable palladium hydride catalyzed intermolecular hydroamination reaction for vinylarenes has been developed. The metal hydride catalyst was prepared by treating PdLCl2 (L=ligand) with AgOTf (OTf=trifluoromethanesulfonate) and (EtO)2MeSiH as the hydride source. The optimized reaction conditions were employed for the hydroamination of various styrenes with anilines, sulfonamides, and indoles. Chiral ligands such as 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (BINAP) gave enantioenriched products in good to excellent yields.

KW - C−N bond formation

KW - enantioselectivity

KW - hydrides

KW - hydroamination

KW - palladium

UR - https://www.scopus.com/pages/publications/85042139251

U2 - 10.1002/ajoc.201700636

DO - 10.1002/ajoc.201700636

M3 - Article

AN - SCOPUS:85042139251

SN - 2193-5807

VL - 7

SP - 451

EP - 457

JO - Asian Journal of Organic Chemistry

JF - Asian Journal of Organic Chemistry

IS - 2

ER -

Stable Palladium Hydride Catalyzed Intermolecular Hydroamination of Vinylarenes

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Keywords

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