One-pot, modular approach to functionalized ketones via nucleophilic addition/Buchwald-Hartwig amination strategy

Jorn de Jong; Dorus Heijnen; Hugo Helbert; Ben L. Feringa

doi:10.1039/c8cc08444k

One-pot, modular approach to functionalized ketones via nucleophilic addition/Buchwald-Hartwig amination strategy

Jorn de Jong, Dorus Heijnen, Hugo Helbert, Ben L. Feringa^*

^*Corresponding author for this work

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

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Abstract

A general one-pot procedure for the 1,2-addition of organolithium reagents to amides followed by the Buchwald-Hartwig amination with in situ released lithium amides is presented. In this work amides are used as masked ketones, revealed by the addition of organolithium reagents which generates a lithium amide, suitable for subsequent Buchwald-Hartwig coupling in the presence of a palladium catalyst. This methodology allows for rapid, efficient and atom economic synthesis of aminoarylketones in good yields.

Original language	English
Pages (from-to)	2908-2911
Number of pages	4
Journal	Chemical Communications
Volume	55
Issue number	20
DOIs	https://doi.org/10.1039/c8cc08444k
Publication status	Published - 11-Mar-2019

Keywords

C-N
CATALYZED AMINATION
ARYL CHLORIDES
BROMIDES
INHIBITORS
REAGENTS
IODIDES
AMMONIA

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One-pot, modular approach to functionalized ketones via nucleophilic addition/Buchwald– Hartwig amination strategyFinal publisher's version, 2.31 MBLicence: CC BY-NC

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@article{96a2fe879a824472ad789ee36f3e4a56,

title = "One-pot, modular approach to functionalized ketones via nucleophilic addition/Buchwald-Hartwig amination strategy",

abstract = "A general one-pot procedure for the 1,2-addition of organolithium reagents to amides followed by the Buchwald-Hartwig amination with in situ released lithium amides is presented. In this work amides are used as masked ketones, revealed by the addition of organolithium reagents which generates a lithium amide, suitable for subsequent Buchwald-Hartwig coupling in the presence of a palladium catalyst. This methodology allows for rapid, efficient and atom economic synthesis of aminoarylketones in good yields.",

keywords = "C-N, CATALYZED AMINATION, ARYL CHLORIDES, BROMIDES, INHIBITORS, REAGENTS, IODIDES, AMMONIA",

author = "{de Jong}, Jorn and Dorus Heijnen and Hugo Helbert and Feringa, {Ben L.}",

year = "2019",

month = mar,

day = "11",

doi = "10.1039/c8cc08444k",

language = "English",

volume = "55",

pages = "2908--2911",

journal = "Chemical Communications",

issn = "1359-7345",

publisher = "ROYAL SOC CHEMISTRY",

number = "20",

}

TY - JOUR

T1 - One-pot, modular approach to functionalized ketones via nucleophilic addition/Buchwald-Hartwig amination strategy

AU - de Jong, Jorn

AU - Heijnen, Dorus

AU - Helbert, Hugo

AU - Feringa, Ben L.

PY - 2019/3/11

Y1 - 2019/3/11

N2 - A general one-pot procedure for the 1,2-addition of organolithium reagents to amides followed by the Buchwald-Hartwig amination with in situ released lithium amides is presented. In this work amides are used as masked ketones, revealed by the addition of organolithium reagents which generates a lithium amide, suitable for subsequent Buchwald-Hartwig coupling in the presence of a palladium catalyst. This methodology allows for rapid, efficient and atom economic synthesis of aminoarylketones in good yields.

AB - A general one-pot procedure for the 1,2-addition of organolithium reagents to amides followed by the Buchwald-Hartwig amination with in situ released lithium amides is presented. In this work amides are used as masked ketones, revealed by the addition of organolithium reagents which generates a lithium amide, suitable for subsequent Buchwald-Hartwig coupling in the presence of a palladium catalyst. This methodology allows for rapid, efficient and atom economic synthesis of aminoarylketones in good yields.

KW - C-N

KW - CATALYZED AMINATION

KW - ARYL CHLORIDES

KW - BROMIDES

KW - INHIBITORS

KW - REAGENTS

KW - IODIDES

KW - AMMONIA

U2 - 10.1039/c8cc08444k

DO - 10.1039/c8cc08444k

M3 - Article

SN - 1359-7345

VL - 55

SP - 2908

EP - 2911

JO - Chemical Communications

JF - Chemical Communications

IS - 20

ER -

One-pot, modular approach to functionalized ketones via nucleophilic addition/Buchwald-Hartwig amination strategy

Abstract

Keywords

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