Chiral Birch reduced tertiary phosphines: Precursors to asymmetric 1,2-cyclohexenebis(tertiary phosphines)

Michelle Bulbrook; Minghui Chu; Karen Deane; Roy J. Doyle; Justina Hinc; Charlotte Peterson; Geoffrey Salem; Nadia Thorman; Anthony C. Willis

doi:10.1039/c0dt00648c

Chiral Birch reduced tertiary phosphines: Precursors to asymmetric 1,2-cyclohexenebis(tertiary phosphines)

Michelle Bulbrook^*, Minghui Chu, Karen Deane, Roy J. Doyle, Justina Hinc, Charlotte Peterson, Geoffrey Salem, Nadia Thorman, Anthony C. Willis

^*Corresponding author for this work

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

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Abstract

The first examples of an optically active Birch reduced tertiary phosphine, viz. (R_P)-(cyclohexa-2,5-dienyl)(3-pentyl)phenylphosphine, and successful hydrophosphination of the related racemic ligand (±)- (cyclohexa-2,5-dienyl)(2-propyl)phenylphosphine with PHPh₂ in the presence of KOBu^t in thf to give a 1,2-cyclohexenebis(tertiary phosphine), viz. (±)-1,2-C₆H₈(PPh ₂)(PPhPrⁱ), are described; as confirmed by crystal structure determinations of [SP-4-4-(S_P,S)]-chloro[(cyclohexa-2,5- dienyl)(3-pentyl)phenylphosphine][2-{1-(dimethylamino)ethyl}phenyl-C,N] palladium(II) and [SP-4-3-(±)]-dimethyl[(1-diphenylphosphino)(2- isopropylphenylphosphino)cyclohexene]platinum(II).

Original language	English
Pages (from-to)	8878-8881
Number of pages	4
Journal	Dalton Transactions
Volume	39
Issue number	38
DOIs	https://doi.org/10.1039/c0dt00648c
Publication status	Published - 14 Oct 2010

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@article{a7b0298a26bd458092ea3268d698c65d,

title = "Chiral Birch reduced tertiary phosphines: Precursors to asymmetric 1,2-cyclohexenebis(tertiary phosphines)",

abstract = "The first examples of an optically active Birch reduced tertiary phosphine, viz. (RP)-(cyclohexa-2,5-dienyl)(3-pentyl)phenylphosphine, and successful hydrophosphination of the related racemic ligand (±)- (cyclohexa-2,5-dienyl)(2-propyl)phenylphosphine with PHPh2 in the presence of KOBut in thf to give a 1,2-cyclohexenebis(tertiary phosphine), viz. (±)-1,2-C6H8(PPh 2)(PPhPri), are described; as confirmed by crystal structure determinations of [SP-4-4-(SP,S)]-chloro[(cyclohexa-2,5- dienyl)(3-pentyl)phenylphosphine][2-{1-(dimethylamino)ethyl}phenyl-C,N] palladium(II) and [SP-4-3-(±)]-dimethyl[(1-diphenylphosphino)(2- isopropylphenylphosphino)cyclohexene]platinum(II).",

author = "Michelle Bulbrook and Minghui Chu and Karen Deane and Doyle, {Roy J.} and Justina Hinc and Charlotte Peterson and Geoffrey Salem and Nadia Thorman and Willis, {Anthony C.}",

year = "2010",

month = oct,

day = "14",

doi = "10.1039/c0dt00648c",

language = "English",

volume = "39",

pages = "8878--8881",

journal = "Dalton Transactions",

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publisher = "Royal Society of Chemistry",

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TY - JOUR

T1 - Chiral Birch reduced tertiary phosphines

T2 - Precursors to asymmetric 1,2-cyclohexenebis(tertiary phosphines)

AU - Bulbrook, Michelle

AU - Chu, Minghui

AU - Deane, Karen

AU - Doyle, Roy J.

AU - Hinc, Justina

AU - Peterson, Charlotte

AU - Salem, Geoffrey

AU - Thorman, Nadia

AU - Willis, Anthony C.

PY - 2010/10/14

Y1 - 2010/10/14

N2 - The first examples of an optically active Birch reduced tertiary phosphine, viz. (RP)-(cyclohexa-2,5-dienyl)(3-pentyl)phenylphosphine, and successful hydrophosphination of the related racemic ligand (±)- (cyclohexa-2,5-dienyl)(2-propyl)phenylphosphine with PHPh2 in the presence of KOBut in thf to give a 1,2-cyclohexenebis(tertiary phosphine), viz. (±)-1,2-C6H8(PPh 2)(PPhPri), are described; as confirmed by crystal structure determinations of [SP-4-4-(SP,S)]-chloro[(cyclohexa-2,5- dienyl)(3-pentyl)phenylphosphine][2-{1-(dimethylamino)ethyl}phenyl-C,N] palladium(II) and [SP-4-3-(±)]-dimethyl[(1-diphenylphosphino)(2- isopropylphenylphosphino)cyclohexene]platinum(II).

AB - The first examples of an optically active Birch reduced tertiary phosphine, viz. (RP)-(cyclohexa-2,5-dienyl)(3-pentyl)phenylphosphine, and successful hydrophosphination of the related racemic ligand (±)- (cyclohexa-2,5-dienyl)(2-propyl)phenylphosphine with PHPh2 in the presence of KOBut in thf to give a 1,2-cyclohexenebis(tertiary phosphine), viz. (±)-1,2-C6H8(PPh 2)(PPhPri), are described; as confirmed by crystal structure determinations of [SP-4-4-(SP,S)]-chloro[(cyclohexa-2,5- dienyl)(3-pentyl)phenylphosphine][2-{1-(dimethylamino)ethyl}phenyl-C,N] palladium(II) and [SP-4-3-(±)]-dimethyl[(1-diphenylphosphino)(2- isopropylphenylphosphino)cyclohexene]platinum(II).

UR - http://www.scopus.com/inward/record.url?scp=77956927738&partnerID=8YFLogxK

U2 - 10.1039/c0dt00648c

DO - 10.1039/c0dt00648c

M3 - Article

SN - 1477-9226

VL - 39

SP - 8878

EP - 8881

JO - Dalton Transactions

JF - Dalton Transactions

IS - 38

ER -

Chiral Birch reduced tertiary phosphines: Precursors to asymmetric 1,2-cyclohexenebis(tertiary phosphines)

Abstract

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