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)

Dalton Trans. 2010 Oct 14;39(38):8878-81. doi: 10.1039/c0dt00648c. Epub 2010 Aug 19.

Authors

Michelle Bulbrook¹, Minghui Chu, Karen Deane, Roy J Doyle, Justina Hinc, Charlotte Peterson, Geoffrey Salem, Nadia Thorman, Anthony C Willis

Affiliation

¹ Research School of Chemistry, College of Physical Sciences, Australian National University, Canberra, ACT 0200, Australia.

PMID: 20721396
DOI: 10.1039/c0dt00648c

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-isopropylphenylphosphino)cyclohexene]platinum(II).