Co(III)-porphyrin-mediated highly regioselective ring-opening of terminal epoxides with alcohols and phenols

Krishnan Venkatasubbaiah; Xunjin Zhu; Elizabeth Kays; Kenneth I. Hardcastle; Christopher W. Jones

doi:10.1021/cs200114x

Co(III)-porphyrin-mediated highly regioselective ring-opening of terminal epoxides with alcohols and phenols

Krishnan Venkatasubbaiah, Xunjin Zhu, Elizabeth Kays, Kenneth I. Hardcastle, Christopher W. Jones

Department of Chemistry

Research output: Contribution to journal › Journal article › peer-review

48 Citations (Scopus)

Abstract

Co-T(p-OMe)PP-SbF₆ (1-SbF₆, T(p-OMe)PP = 5,10,15,20-tetrakis(4-methoxyphenyl)porphyrinato) is demonstrated to be a highly active and regioselective catalyst in the ring-opening of various epoxides with alcohols and phenols. 1-SbF₆ is demonstrated to be twice as active as the established Co-salen-SbF₆ (2-SbF₆, salen = trans-N,N-bis(3,5-ditertbutylsalicylidene)-1,2-cyclohexanediamine) catalyst, exhibiting >99% regioselectivity in many cases. The catalyst is suggested to promote the ring-opening via a cooperative bimolecular mechanism because the Co-porphyrin dimer, 1d-OTs, is significantly more active compared with the monomeric catalyst, 1-OTs.

Original language	English
Pages (from-to)	489-492
Number of pages	4
Journal	ACS Catalysis
Volume	1
Issue number	5
DOIs	https://doi.org/10.1021/cs200114x
Publication status	Published - 6 May 2011

Scopus Subject Areas

Catalysis
General Chemistry

User-Defined Keywords

α -aryloxy alcohols
α-alkoxy alcohols
co-porphyrin
epoxides
ring-opening

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10.1021/cs200114x

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@article{d61aebda57f448ada2645ed98c3618ce,

title = "Co(III)-porphyrin-mediated highly regioselective ring-opening of terminal epoxides with alcohols and phenols",

abstract = "Co-T(p-OMe)PP-SbF6 (1-SbF6, T(p-OMe)PP = 5,10,15,20-tetrakis(4-methoxyphenyl)porphyrinato) is demonstrated to be a highly active and regioselective catalyst in the ring-opening of various epoxides with alcohols and phenols. 1-SbF6 is demonstrated to be twice as active as the established Co-salen-SbF6 (2-SbF6, salen = trans-N,N-bis(3,5-ditertbutylsalicylidene)-1,2-cyclohexanediamine) catalyst, exhibiting >99% regioselectivity in many cases. The catalyst is suggested to promote the ring-opening via a cooperative bimolecular mechanism because the Co-porphyrin dimer, 1d-OTs, is significantly more active compared with the monomeric catalyst, 1-OTs.",

keywords = "α -aryloxy alcohols, α-alkoxy alcohols, co-porphyrin, epoxides, ring-opening",

author = "Krishnan Venkatasubbaiah and Xunjin Zhu and Elizabeth Kays and Hardcastle, {Kenneth I.} and Jones, {Christopher W.}",

note = "DowChemical is acknowledged for funding this work. ",

year = "2011",

month = may,

day = "6",

doi = "10.1021/cs200114x",

language = "English",

volume = "1",

pages = "489--492",

journal = "ACS Catalysis",

issn = "2155-5435",

publisher = "American Chemical Society",

number = "5",

}

TY - JOUR

T1 - Co(III)-porphyrin-mediated highly regioselective ring-opening of terminal epoxides with alcohols and phenols

AU - Venkatasubbaiah, Krishnan

AU - Zhu, Xunjin

AU - Kays, Elizabeth

AU - Hardcastle, Kenneth I.

AU - Jones, Christopher W.

N1 - DowChemical is acknowledged for funding this work.

PY - 2011/5/6

Y1 - 2011/5/6

N2 - Co-T(p-OMe)PP-SbF6 (1-SbF6, T(p-OMe)PP = 5,10,15,20-tetrakis(4-methoxyphenyl)porphyrinato) is demonstrated to be a highly active and regioselective catalyst in the ring-opening of various epoxides with alcohols and phenols. 1-SbF6 is demonstrated to be twice as active as the established Co-salen-SbF6 (2-SbF6, salen = trans-N,N-bis(3,5-ditertbutylsalicylidene)-1,2-cyclohexanediamine) catalyst, exhibiting >99% regioselectivity in many cases. The catalyst is suggested to promote the ring-opening via a cooperative bimolecular mechanism because the Co-porphyrin dimer, 1d-OTs, is significantly more active compared with the monomeric catalyst, 1-OTs.

AB - Co-T(p-OMe)PP-SbF6 (1-SbF6, T(p-OMe)PP = 5,10,15,20-tetrakis(4-methoxyphenyl)porphyrinato) is demonstrated to be a highly active and regioselective catalyst in the ring-opening of various epoxides with alcohols and phenols. 1-SbF6 is demonstrated to be twice as active as the established Co-salen-SbF6 (2-SbF6, salen = trans-N,N-bis(3,5-ditertbutylsalicylidene)-1,2-cyclohexanediamine) catalyst, exhibiting >99% regioselectivity in many cases. The catalyst is suggested to promote the ring-opening via a cooperative bimolecular mechanism because the Co-porphyrin dimer, 1d-OTs, is significantly more active compared with the monomeric catalyst, 1-OTs.

KW - α -aryloxy alcohols

KW - α-alkoxy alcohols

KW - co-porphyrin

KW - epoxides

KW - ring-opening

UR - http://www.scopus.com/inward/record.url?scp=79955920741&partnerID=8YFLogxK

U2 - 10.1021/cs200114x

DO - 10.1021/cs200114x

M3 - Journal article

AN - SCOPUS:79955920741

SN - 2155-5435

VL - 1

SP - 489

EP - 492

JO - ACS Catalysis

JF - ACS Catalysis

IS - 5

ER -

Co(III)-porphyrin-mediated highly regioselective ring-opening of terminal epoxides with alcohols and phenols

Abstract

Scopus Subject Areas

User-Defined Keywords

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