Platinum-catalysed 1,4-diboration of 1,3-dienes

William Clegg; Thorsten R.F. Johann; Todd B. Marder; Nicholas C. Norman; A. Guy Orpen; Torren M. Peakman; Michael J. Quayle; Craig R. Rice; Andrew J. Scott

doi:10.1039/a800108a

Platinum-catalysed 1,4-diboration of 1,3-dienes

William Clegg, Thorsten R.F. Johann, Todd B. Marder, Nicholas C. Norman, A. Guy Orpen, Torren M. Peakman, Michael J. Quayle, Craig R. Rice, Andrew J. Scott

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

84 Citations (Scopus)

Abstract

The chiral diborane(4) compounds B₂[R,R-O₂CH(CO₂Me)CH(CO₂Me)] ₂, B₂(S,O₂CH₂CHPh)₂, B₂(R,R-O₂-CHPhCHPh)₂ and B₂(O₂C₂₀H¹²)₂ (O₂C₂₀H₁₂ = 1,7′-bi-2-naphtholate) have been synthesized. All four compounds have been characterised by X-ray crystallography, the latter as a racemate. The B-B bond oxidativeaddition reactions of the first three compounds with [Pt(PPh₃)₂(μ-C₂H₄)] resulted in the platinum(II) bis(boryl) complexes cis-[Pt(PPh₃)₂{B[R,R-O₂CH(CO ₂Me)CH(CO₂Me)]}₂], cis-[Pt(PPh₃)₂{B(S-O₂CH₂CHPh)} ₂] and cis-[Pt(PPh₃)₂{B(R,R-O₂CHPhCHPh)}₂]; the former two were also characterised by X-ray crystallography. The platinum-catalysed diborations of a range of prochiral 1,3-dienes with the compounds B₂[R,R-O₂CH(CO₂Me)-CH(CO₂Me)] ₂, B₂(S-O₂CH₂CHPh)₂ and B₂(R,R-O₂CHPhCHPh)₂ were studied. Although these reactions were clean and quantitative, observed product d.e.s (measured by ¹H NMR spectroscopy) were low or non-existent indicating that chirality transfer from the diborane(4) diolate groups to the diene diboration product is not efficient in these cases.

Original language	English
Pages (from-to)	1431-1438
Number of pages	8
Journal	Journal of the Chemical Society - Dalton Transactions
Issue number	9
DOIs	https://doi.org/10.1039/a800108a
Publication status	Published - 7 May 1998
Externally published	Yes

Access to Document

10.1039/a800108a

Cite this

@article{da3532934cad4a9397cc5d7480ef9b0f,

title = "Platinum-catalysed 1,4-diboration of 1,3-dienes",

abstract = "The chiral diborane(4) compounds B2[R,R-O2CH(CO2Me)CH(CO2Me)] 2, B2(S,O2CH2CHPh)2, B2(R,R-O2-CHPhCHPh)2 and B2(O2C20H12)2 (O2C20H12 = 1,7′-bi-2-naphtholate) have been synthesized. All four compounds have been characterised by X-ray crystallography, the latter as a racemate. The B-B bond oxidativeaddition reactions of the first three compounds with [Pt(PPh3)2(μ-C2H4)] resulted in the platinum(II) bis(boryl) complexes cis-[Pt(PPh3)2{B[R,R-O2CH(CO 2Me)CH(CO2Me)]}2], cis-[Pt(PPh3)2{B(S-O2CH2CHPh)} 2] and cis-[Pt(PPh3)2{B(R,R-O2CHPhCHPh)}2]; the former two were also characterised by X-ray crystallography. The platinum-catalysed diborations of a range of prochiral 1,3-dienes with the compounds B2[R,R-O2CH(CO2Me)-CH(CO2Me)] 2, B2(S-O2CH2CHPh)2 and B2(R,R-O2CHPhCHPh)2 were studied. Although these reactions were clean and quantitative, observed product d.e.s (measured by 1H NMR spectroscopy) were low or non-existent indicating that chirality transfer from the diborane(4) diolate groups to the diene diboration product is not efficient in these cases.",

author = "William Clegg and Johann, {Thorsten R.F.} and Marder, {Todd B.} and Norman, {Nicholas C.} and Orpen, {A. Guy} and Peakman, {Torren M.} and Quayle, {Michael J.} and Rice, {Craig R.} and Scott, {Andrew J.}",

year = "1998",

month = may,

day = "7",

doi = "10.1039/a800108a",

language = "English",

pages = "1431--1438",

journal = "Dalton Transactions",

issn = "1477-9226",

publisher = "Royal Society of Chemistry",

number = "9",

}

TY - JOUR

T1 - Platinum-catalysed 1,4-diboration of 1,3-dienes

AU - Clegg, William

AU - Johann, Thorsten R.F.

AU - Marder, Todd B.

AU - Norman, Nicholas C.

AU - Orpen, A. Guy

AU - Peakman, Torren M.

AU - Quayle, Michael J.

AU - Rice, Craig R.

AU - Scott, Andrew J.

PY - 1998/5/7

Y1 - 1998/5/7

N2 - The chiral diborane(4) compounds B2[R,R-O2CH(CO2Me)CH(CO2Me)] 2, B2(S,O2CH2CHPh)2, B2(R,R-O2-CHPhCHPh)2 and B2(O2C20H12)2 (O2C20H12 = 1,7′-bi-2-naphtholate) have been synthesized. All four compounds have been characterised by X-ray crystallography, the latter as a racemate. The B-B bond oxidativeaddition reactions of the first three compounds with [Pt(PPh3)2(μ-C2H4)] resulted in the platinum(II) bis(boryl) complexes cis-[Pt(PPh3)2{B[R,R-O2CH(CO 2Me)CH(CO2Me)]}2], cis-[Pt(PPh3)2{B(S-O2CH2CHPh)} 2] and cis-[Pt(PPh3)2{B(R,R-O2CHPhCHPh)}2]; the former two were also characterised by X-ray crystallography. The platinum-catalysed diborations of a range of prochiral 1,3-dienes with the compounds B2[R,R-O2CH(CO2Me)-CH(CO2Me)] 2, B2(S-O2CH2CHPh)2 and B2(R,R-O2CHPhCHPh)2 were studied. Although these reactions were clean and quantitative, observed product d.e.s (measured by 1H NMR spectroscopy) were low or non-existent indicating that chirality transfer from the diborane(4) diolate groups to the diene diboration product is not efficient in these cases.

AB - The chiral diborane(4) compounds B2[R,R-O2CH(CO2Me)CH(CO2Me)] 2, B2(S,O2CH2CHPh)2, B2(R,R-O2-CHPhCHPh)2 and B2(O2C20H12)2 (O2C20H12 = 1,7′-bi-2-naphtholate) have been synthesized. All four compounds have been characterised by X-ray crystallography, the latter as a racemate. The B-B bond oxidativeaddition reactions of the first three compounds with [Pt(PPh3)2(μ-C2H4)] resulted in the platinum(II) bis(boryl) complexes cis-[Pt(PPh3)2{B[R,R-O2CH(CO 2Me)CH(CO2Me)]}2], cis-[Pt(PPh3)2{B(S-O2CH2CHPh)} 2] and cis-[Pt(PPh3)2{B(R,R-O2CHPhCHPh)}2]; the former two were also characterised by X-ray crystallography. The platinum-catalysed diborations of a range of prochiral 1,3-dienes with the compounds B2[R,R-O2CH(CO2Me)-CH(CO2Me)] 2, B2(S-O2CH2CHPh)2 and B2(R,R-O2CHPhCHPh)2 were studied. Although these reactions were clean and quantitative, observed product d.e.s (measured by 1H NMR spectroscopy) were low or non-existent indicating that chirality transfer from the diborane(4) diolate groups to the diene diboration product is not efficient in these cases.

UR - http://www.scopus.com/inward/record.url?scp=33748503927&partnerID=8YFLogxK

U2 - 10.1039/a800108a

DO - 10.1039/a800108a

M3 - Article

AN - SCOPUS:33748503927

SP - 1431

EP - 1438

JO - Dalton Transactions

JF - Dalton Transactions

SN - 1477-9226

IS - 9

ER -

Platinum-catalysed 1,4-diboration of 1,3-dienes

Abstract

Access to Document

Other files and links

Fingerprint

Cite this