Addition of boranes to (E)-(η5-C5H5)2Zr(CH=CHPh)Cl

• Authors: Patrick Ferland , Kathleen Prosser , Jeremy Bourque , Ian Edwards , Nathan Hamilton , Lori Joyce , Mathew Finniss , Scott Yorke , Christopher Vogels , Frédéric-Georges Fontaine , Andreas Decken , Stephen Westcott
• Languages of publication: EN

Abstracts

EN

In this study, the addition of boranes to (E)-(η5-C5H5)2Zr(CH=CHPh)Cl (3) has been examined in order to investigate the regioselectivity of these ‘hydroboration’ reactions. We have found that these additions proceed with remarkable selectivity to give exclusive formation of a saturated organic molecule where one carbon atom has both the boron and the zirconium fragments. These reactions do not proceed via a conventional hydroboration reaction, but instead go through an initial transmetalation step to generate (E)-(η5-C5H5)2Zr(H)Cl (1) and the corresponding alkenyl boron intermediate, whereupon subsequent hydrozirconation of this latter species gives the geminal products. An x-ray diffraction study has been conducted on gem-(η5-C5H5)2Zr(CH(Bpin)CH2Ph)Cl (pin = 1, 2-O2C2Me4) (2). Crystals of 2 were orthorhombic with a = 18.545(3) Å, b = 15.713(3) Å, c = 16.157(3) Å in the space group Pccn. An x-ray diffraction study has also been conducted on the trinuclear zirconium oxide species (η5-C5H5)2ZrO2[ZrCl(η5-C5H5)2]2(4). Crystals of 4 were orthorhombic with a = 13.6000(8) Å, b = 14.2252(8) Å, c = 17.6500(10) Å in the space group P2(1)2(1)2(1). [...]

Keywords

EN

Boron; Hydroboration; Hydrozirconation; Regioselectivity; Transmetalation

• Publisher: De Gruyter Open
• Journal: Open Chemistry
• Year: 2013
• Volume: 11
• Issue: 5
• Pages: 811-816

Dates

published

1 - 5 - 2013

online

27 - 2 - 2013

Contributors

author

Patrick Ferland

• Department of Chemistry, Centre for Research on the Properties of Interfaces and Catalysis (CERPIC), University of Laval, Québec City, Québec, G1V 0A6, Canada

author

Kathleen Prosser

• Department of Chemistry and Biochemistry, Mount Allison University, Sackville, New Brunswick, E4L 1G8, Canada

author

Jeremy Bourque

• Department of Chemistry and Biochemistry, Mount Allison University, Sackville, New Brunswick, E4L 1G8, Canada

author

Ian Edwards

• Department of Chemistry and Biochemistry, Mount Allison University, Sackville, New Brunswick, E4L 1G8, Canada

author

Nathan Hamilton

• Department of Chemistry and Biochemistry, Mount Allison University, Sackville, New Brunswick, E4L 1G8, Canada

author

Lori Joyce

• Department of Chemistry and Biochemistry, Mount Allison University, Sackville, New Brunswick, E4L 1G8, Canada

author

Mathew Finniss

• Department of Chemistry and Biochemistry, Mount Allison University, Sackville, New Brunswick, E4L 1G8, Canada

author

Scott Yorke

• Department of Chemistry and Biochemistry, Mount Allison University, Sackville, New Brunswick, E4L 1G8, Canada

author

Christopher Vogels

• Department of Chemistry and Biochemistry, Mount Allison University, Sackville, New Brunswick, E4L 1G8, Canada

author

Frédéric-Georges Fontaine

• Department of Chemistry, Centre for Research on the Properties of Interfaces and Catalysis (CERPIC), University of Laval, Québec City, Québec, G1V 0A6, Canada

author

Andreas Decken

• Department of Chemistry, University of New Brunswick, Fredericton, New Brunswick, E3B 5A3, Canada

author

Stephen Westcott

• Department of Chemistry and Biochemistry, Mount Allison University, Sackville, New Brunswick, E4L 1G8, Canada

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Identifiers

DOI

10.2478/s11532-013-0216-5