Hydrogen Bond-Accelerated meta-Selective C-H Borylation of Aromatic Compounds and Expression of Functional Group and Substrate Specificities

Xu Lu, Yusuke Yoshigoe, Haruka Ida, Mitsumi Nishi, Motomu Kanai, Yoichiro Kuninobu

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

We found that meta-selective C-H borylation of aromatic compounds was accelerated when using urea moiety-containing bipyridine-type ligands unlike in cases involving a bipyridine-type ligand without the urea moiety. The acceleration was due to the recognition and capture of the aromatic substrates by the urea moiety of the ligand by hydrogen bonding. The acceleration was further enhanced by modifying the electronic and steric properties of the ligand. The functional group and substrate specificities were also observed using the urea moiety-containing ligands.

Original languageEnglish
Pages (from-to)1705-1709
Number of pages5
JournalACS Catalysis
Volume9
Issue number3
DOIs
Publication statusPublished - Mar 1 2019

Fingerprint

Aromatic compounds
Functional groups
Hydrogen bonds
Urea
Ligands
Substrates

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)

Cite this

Hydrogen Bond-Accelerated meta-Selective C-H Borylation of Aromatic Compounds and Expression of Functional Group and Substrate Specificities. / Lu, Xu; Yoshigoe, Yusuke; Ida, Haruka; Nishi, Mitsumi; Kanai, Motomu; Kuninobu, Yoichiro.

In: ACS Catalysis, Vol. 9, No. 3, 01.03.2019, p. 1705-1709.

Research output: Contribution to journalArticle

Lu, Xu ; Yoshigoe, Yusuke ; Ida, Haruka ; Nishi, Mitsumi ; Kanai, Motomu ; Kuninobu, Yoichiro. / Hydrogen Bond-Accelerated meta-Selective C-H Borylation of Aromatic Compounds and Expression of Functional Group and Substrate Specificities. In: ACS Catalysis. 2019 ; Vol. 9, No. 3. pp. 1705-1709.
@article{f43077168e7a4a09bb4b048b68f6ee59,
title = "Hydrogen Bond-Accelerated meta-Selective C-H Borylation of Aromatic Compounds and Expression of Functional Group and Substrate Specificities",
abstract = "We found that meta-selective C-H borylation of aromatic compounds was accelerated when using urea moiety-containing bipyridine-type ligands unlike in cases involving a bipyridine-type ligand without the urea moiety. The acceleration was due to the recognition and capture of the aromatic substrates by the urea moiety of the ligand by hydrogen bonding. The acceleration was further enhanced by modifying the electronic and steric properties of the ligand. The functional group and substrate specificities were also observed using the urea moiety-containing ligands.",
author = "Xu Lu and Yusuke Yoshigoe and Haruka Ida and Mitsumi Nishi and Motomu Kanai and Yoichiro Kuninobu",
year = "2019",
month = "3",
day = "1",
doi = "10.1021/acscatal.8b05005",
language = "English",
volume = "9",
pages = "1705--1709",
journal = "ACS Catalysis",
issn = "2155-5435",
publisher = "American Chemical Society",
number = "3",

}

TY - JOUR

T1 - Hydrogen Bond-Accelerated meta-Selective C-H Borylation of Aromatic Compounds and Expression of Functional Group and Substrate Specificities

AU - Lu, Xu

AU - Yoshigoe, Yusuke

AU - Ida, Haruka

AU - Nishi, Mitsumi

AU - Kanai, Motomu

AU - Kuninobu, Yoichiro

PY - 2019/3/1

Y1 - 2019/3/1

N2 - We found that meta-selective C-H borylation of aromatic compounds was accelerated when using urea moiety-containing bipyridine-type ligands unlike in cases involving a bipyridine-type ligand without the urea moiety. The acceleration was due to the recognition and capture of the aromatic substrates by the urea moiety of the ligand by hydrogen bonding. The acceleration was further enhanced by modifying the electronic and steric properties of the ligand. The functional group and substrate specificities were also observed using the urea moiety-containing ligands.

AB - We found that meta-selective C-H borylation of aromatic compounds was accelerated when using urea moiety-containing bipyridine-type ligands unlike in cases involving a bipyridine-type ligand without the urea moiety. The acceleration was due to the recognition and capture of the aromatic substrates by the urea moiety of the ligand by hydrogen bonding. The acceleration was further enhanced by modifying the electronic and steric properties of the ligand. The functional group and substrate specificities were also observed using the urea moiety-containing ligands.

UR - http://www.scopus.com/inward/record.url?scp=85062417210&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85062417210&partnerID=8YFLogxK

U2 - 10.1021/acscatal.8b05005

DO - 10.1021/acscatal.8b05005

M3 - Article

VL - 9

SP - 1705

EP - 1709

JO - ACS Catalysis

JF - ACS Catalysis

SN - 2155-5435

IS - 3

ER -