Efficient 1,4-addition of enones and boronic acids catalyzed by a Ni-Zn hydroxyl double salt-intercalated anionic rhodium(III) complex

Takayoshi Hara, Nozomi Fujita, Nobuyuki Ichikuni, Karen Wilson, Adam F. Lee, Shogo Shimazu*

*Corresponding author for this work

Research output: Contribution to journalArticle

Abstract

Intercalation of an in situ prepared [Rh(OH)6]3- complex into an anion exchangeable Ni-Zn layered hydroxy double salt (Rh/NiZn) was demonstrated. The resulting Rh/NiZn effectively catalyzed the 1,4-addition of diverse enones and phenylboronic acids to their corresponding β-substituted carbonyl compounds. In the case of 2-cyclohexen-1-one and phenylboronic acid, a turnover frequency (TOF) of 920 h-1 based on Rh was achieved. The [Rh(OH)6]3- complex maintained its original monomeric trivalent state within the NiZn interlayer following catalysis, attributable to a strong electrostatic interaction between the NiZn host and anionic Rh(III) complex.

Original languageEnglish
Pages (from-to)4040-4046
Number of pages7
JournalACS Catalysis
Volume4
Issue number11
Early online date6 Oct 2014
DOIs
Publication statusPublished - 7 Nov 2014

Fingerprint

Boronic Acids
Rhodium
Hydroxyl Radical
Salts
Carbonyl compounds
Acids
Intercalation
Coulomb interactions
Catalysis
Anions
Negative ions
benzeneboronic acid
2-cyclohexen-1-one

Bibliographical note

Funding: Grant-in-Aid for Scientific Research from the Ministry of Education, Culture, Sports, Science, and Technology of Japan (25420824); Photon Factory (KEK-PF, Proposal No. 2012G596; EPSRC (EP/G007594/4); and Royal
Society (Industry Fellowship).

Keywords

  • 1,4-addition
  • anion exchange
  • intercalation
  • Ni-Zn hydroxyl double salt
  • rhodium

Cite this

Hara, Takayoshi ; Fujita, Nozomi ; Ichikuni, Nobuyuki ; Wilson, Karen ; Lee, Adam F. ; Shimazu, Shogo. / Efficient 1,4-addition of enones and boronic acids catalyzed by a Ni-Zn hydroxyl double salt-intercalated anionic rhodium(III) complex. In: ACS Catalysis. 2014 ; Vol. 4, No. 11. pp. 4040-4046.
@article{014ca315ed69433baa750c0a6bf442f4,
title = "Efficient 1,4-addition of enones and boronic acids catalyzed by a Ni-Zn hydroxyl double salt-intercalated anionic rhodium(III) complex",
abstract = "Intercalation of an in situ prepared [Rh(OH)6]3- complex into an anion exchangeable Ni-Zn layered hydroxy double salt (Rh/NiZn) was demonstrated. The resulting Rh/NiZn effectively catalyzed the 1,4-addition of diverse enones and phenylboronic acids to their corresponding β-substituted carbonyl compounds. In the case of 2-cyclohexen-1-one and phenylboronic acid, a turnover frequency (TOF) of 920 h-1 based on Rh was achieved. The [Rh(OH)6]3- complex maintained its original monomeric trivalent state within the NiZn interlayer following catalysis, attributable to a strong electrostatic interaction between the NiZn host and anionic Rh(III) complex.",
keywords = "1,4-addition, anion exchange, intercalation, Ni-Zn hydroxyl double salt, rhodium",
author = "Takayoshi Hara and Nozomi Fujita and Nobuyuki Ichikuni and Karen Wilson and Lee, {Adam F.} and Shogo Shimazu",
note = "Funding: Grant-in-Aid for Scientific Research from the Ministry of Education, Culture, Sports, Science, and Technology of Japan (25420824); Photon Factory (KEK-PF, Proposal No. 2012G596; EPSRC (EP/G007594/4); and Royal Society (Industry Fellowship).",
year = "2014",
month = "11",
day = "7",
doi = "10.1021/cs501267h",
language = "English",
volume = "4",
pages = "4040--4046",
journal = "ACS Catalysis",
issn = "2155-5435",
publisher = "American Chemical Society",
number = "11",

}

Efficient 1,4-addition of enones and boronic acids catalyzed by a Ni-Zn hydroxyl double salt-intercalated anionic rhodium(III) complex. / Hara, Takayoshi; Fujita, Nozomi; Ichikuni, Nobuyuki; Wilson, Karen; Lee, Adam F.; Shimazu, Shogo.

In: ACS Catalysis, Vol. 4, No. 11, 07.11.2014, p. 4040-4046.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Efficient 1,4-addition of enones and boronic acids catalyzed by a Ni-Zn hydroxyl double salt-intercalated anionic rhodium(III) complex

AU - Hara, Takayoshi

AU - Fujita, Nozomi

AU - Ichikuni, Nobuyuki

AU - Wilson, Karen

AU - Lee, Adam F.

AU - Shimazu, Shogo

N1 - Funding: Grant-in-Aid for Scientific Research from the Ministry of Education, Culture, Sports, Science, and Technology of Japan (25420824); Photon Factory (KEK-PF, Proposal No. 2012G596; EPSRC (EP/G007594/4); and Royal Society (Industry Fellowship).

PY - 2014/11/7

Y1 - 2014/11/7

N2 - Intercalation of an in situ prepared [Rh(OH)6]3- complex into an anion exchangeable Ni-Zn layered hydroxy double salt (Rh/NiZn) was demonstrated. The resulting Rh/NiZn effectively catalyzed the 1,4-addition of diverse enones and phenylboronic acids to their corresponding β-substituted carbonyl compounds. In the case of 2-cyclohexen-1-one and phenylboronic acid, a turnover frequency (TOF) of 920 h-1 based on Rh was achieved. The [Rh(OH)6]3- complex maintained its original monomeric trivalent state within the NiZn interlayer following catalysis, attributable to a strong electrostatic interaction between the NiZn host and anionic Rh(III) complex.

AB - Intercalation of an in situ prepared [Rh(OH)6]3- complex into an anion exchangeable Ni-Zn layered hydroxy double salt (Rh/NiZn) was demonstrated. The resulting Rh/NiZn effectively catalyzed the 1,4-addition of diverse enones and phenylboronic acids to their corresponding β-substituted carbonyl compounds. In the case of 2-cyclohexen-1-one and phenylboronic acid, a turnover frequency (TOF) of 920 h-1 based on Rh was achieved. The [Rh(OH)6]3- complex maintained its original monomeric trivalent state within the NiZn interlayer following catalysis, attributable to a strong electrostatic interaction between the NiZn host and anionic Rh(III) complex.

KW - 1,4-addition

KW - anion exchange

KW - intercalation

KW - Ni-Zn hydroxyl double salt

KW - rhodium

UR - http://www.scopus.com/inward/record.url?scp=84982719081&partnerID=8YFLogxK

UR - https://pubs.acs.org/doi/10.1021/cs501267h

U2 - 10.1021/cs501267h

DO - 10.1021/cs501267h

M3 - Article

VL - 4

SP - 4040

EP - 4046

JO - ACS Catalysis

JF - ACS Catalysis

SN - 2155-5435

IS - 11

ER -