Ni-Catalyzed Intermolecular C(sp3)-H Amidation Tuned by Bidentate Directing Groups

Yeong Bum Kim; Joonghee Won; Jeonghyo Lee; Junho Kim; Bingwei Zhou; Jung Woo Park; Mu Hyun Baik; Sukbok Chang

doi:10.1021/acscatal.1c00070

Ni-Catalyzed Intermolecular C(sp³)-H Amidation Tuned by Bidentate Directing Groups

Yeong Bum Kim, Joonghee Won, Jeonghyo Lee, Junho Kim, Bingwei Zhou, Jung Woo Park, Mu Hyun Baik, Sukbok Chang

Dept. of Fine Chemistry

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

33 Scopus citations

Abstract

We disclose herein a directing group-assisted nickel-catalyzed intermolecular C(sp3)-H amidation using organic azides as nitrene precursors. With the installation of an electronically tailored directing group, enhanced amidation efficiency was achieved. A series of experimental and computational studies suggested that a putative nickel(III)-nitrenoid species is a key intermediate in the C-N bond-forming process.

Original language	English
Pages (from-to)	3067-3072
Number of pages	6
Journal	ACS Catalysis
Volume	11
Issue number	5
DOIs	https://doi.org/10.1021/acscatal.1c00070
State	Published - 5 Mar 2021

Keywords

8-aminoquinolines
C(sp)-H amidation
electronic tuning
nickel catalysis
organic azides

Access to Document

10.1021/acscatal.1c00070

Cite this

@article{f512d46f8ce84e19bd6bcd5c5ae74c6a,

title = "Ni-Catalyzed Intermolecular C(sp3)-H Amidation Tuned by Bidentate Directing Groups",

abstract = "We disclose herein a directing group-assisted nickel-catalyzed intermolecular C(sp3)-H amidation using organic azides as nitrene precursors. With the installation of an electronically tailored directing group, enhanced amidation efficiency was achieved. A series of experimental and computational studies suggested that a putative nickel(III)-nitrenoid species is a key intermediate in the C-N bond-forming process.",

keywords = "8-aminoquinolines, C(sp)-H amidation, electronic tuning, nickel catalysis, organic azides",

author = "Kim, \{Yeong Bum\} and Joonghee Won and Jeonghyo Lee and Junho Kim and Bingwei Zhou and Park, \{Jung Woo\} and Baik, \{Mu Hyun\} and Sukbok Chang",

note = "Publisher Copyright: {\textcopyright} 2021 American Chemical Society.",

year = "2021",

month = mar,

day = "5",

doi = "10.1021/acscatal.1c00070",

language = "English",

volume = "11",

pages = "3067--3072",

journal = "ACS Catalysis",

issn = "2155-5435",

number = "5",

}

TY - JOUR

T1 - Ni-Catalyzed Intermolecular C(sp3)-H Amidation Tuned by Bidentate Directing Groups

AU - Kim, Yeong Bum

AU - Won, Joonghee

AU - Lee, Jeonghyo

AU - Kim, Junho

AU - Zhou, Bingwei

AU - Park, Jung Woo

AU - Baik, Mu Hyun

AU - Chang, Sukbok

PY - 2021/3/5

Y1 - 2021/3/5

N2 - We disclose herein a directing group-assisted nickel-catalyzed intermolecular C(sp3)-H amidation using organic azides as nitrene precursors. With the installation of an electronically tailored directing group, enhanced amidation efficiency was achieved. A series of experimental and computational studies suggested that a putative nickel(III)-nitrenoid species is a key intermediate in the C-N bond-forming process.

AB - We disclose herein a directing group-assisted nickel-catalyzed intermolecular C(sp3)-H amidation using organic azides as nitrene precursors. With the installation of an electronically tailored directing group, enhanced amidation efficiency was achieved. A series of experimental and computational studies suggested that a putative nickel(III)-nitrenoid species is a key intermediate in the C-N bond-forming process.

KW - 8-aminoquinolines

KW - C(sp)-H amidation

KW - electronic tuning

KW - nickel catalysis

KW - organic azides

UR - https://www.scopus.com/pages/publications/85101971244

U2 - 10.1021/acscatal.1c00070

DO - 10.1021/acscatal.1c00070

M3 - Article

AN - SCOPUS:85101971244

SN - 2155-5435

VL - 11

SP - 3067

EP - 3072

JO - ACS Catalysis

JF - ACS Catalysis

IS - 5

ER -

Ni-Catalyzed Intermolecular C(sp³)-H Amidation Tuned by Bidentate Directing Groups

Abstract

Keywords

Access to Document

Other files and links

Fingerprint

Cite this