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

doi:10.1021/cs501267h

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

Chiba University

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

22 Citations (Scopus)

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 language	English
Pages (from-to)	4040-4046
Number of pages	7
Journal	ACS Catalysis
Volume	4
Issue number	11
Early online date	6 Oct 2014
DOIs	https://doi.org/10.1021/cs501267h
Publication status	Published - 7 Nov 2014

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

Access to Document

10.1021/cs501267h

Cite this

@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 = nov,

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",

}

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 - https://www.scopus.com/pages/publications/84982719081

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

U2 - 10.1021/cs501267h

DO - 10.1021/cs501267h

M3 - Article

SN - 2155-5435

VL - 4

SP - 4040

EP - 4046

JO - ACS Catalysis

JF - ACS Catalysis

IS - 11

ER -

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

Abstract

Bibliographical note

Keywords

Access to Document

Other files and links

Fingerprint

Cite this