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

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

12 Citations (Scopus)

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 PHPh(2) in the presence of KOBu(t) in thf to give a 1,2-cyclohexenebis(tertiary phosphine), viz. (+/-)-1,2-C(6)H(8)(PPh(2))(PPhPr(i)), 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-isopropyl-phenylphosphino)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 - 2010
Externally published	Yes

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@article{0399f851aaaa4e38909d925004287998,

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. (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 PHPh(2) in the presence of KOBu(t) in thf to give a 1,2-cyclohexenebis(tertiary phosphine), viz. (+/-)-1,2-C(6)H(8)(PPh(2))(PPhPr(i)), 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-isopropyl-phenylphosphino)cyclohexene]platinum(II).",

keywords = "CARBON-PHOSPHORUS BOND, MOLECULAR-STRUCTURE, PALLADIUM(II) COMPLEXES, REDUCTIVE CLEAVAGE, ALKALI-METALS, RESOLUTION, CRYSTAL",

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",

doi = "10.1039/c0dt00648c",

language = "English",

volume = "39",

pages = "8878--8881",

journal = "Dalton Transactions",

issn = "1477-9226",

publisher = "ROYAL SOC CHEMISTRY",

number = "38",

}

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

Y1 - 2010

N2 - 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 PHPh(2) in the presence of KOBu(t) in thf to give a 1,2-cyclohexenebis(tertiary phosphine), viz. (+/-)-1,2-C(6)H(8)(PPh(2))(PPhPr(i)), 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-isopropyl-phenylphosphino)cyclohexene]platinum(II).

AB - 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 PHPh(2) in the presence of KOBu(t) in thf to give a 1,2-cyclohexenebis(tertiary phosphine), viz. (+/-)-1,2-C(6)H(8)(PPh(2))(PPhPr(i)), 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-isopropyl-phenylphosphino)cyclohexene]platinum(II).

KW - CARBON-PHOSPHORUS BOND

KW - MOLECULAR-STRUCTURE

KW - PALLADIUM(II) COMPLEXES

KW - REDUCTIVE CLEAVAGE

KW - ALKALI-METALS

KW - RESOLUTION

KW - CRYSTAL

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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