Research & Faculty

Default Header Image

Catalytic transfer hydrogenation of ketones by the use of ruthenium complexes incorporating the new tridentate ligand, bis(2-oxazolin-2-ylmethyl)phenylphosphine

TitleCatalytic transfer hydrogenation of ketones by the use of ruthenium complexes incorporating the new tridentate ligand, bis(2-oxazolin-2-ylmethyl)phenylphosphine
Publication TypeJournal Article
Year of Publication1999
AuthorsBraunstein, P, Fryzuk, MD, Naud, F, Rettig, SJ
JournalJournal of the Chemical Society-Dalton Transactions
Pagination589-594
Date PublishedFeb
Type of ArticleArticle
ISBN Number0300-9246
KeywordsACETOPHENONE, ASYMMETRIC TRANSFER HYDROGENATION, chiral ligands, PROPAN-2-OL
Abstract

The new heterofunctional phosphine ligand bis(2-oxazolin-2-ylmethyl)phenylphosphine (N,P,N) has been prepared and has allowed the synthesis of the ruthenium complexes fac-[RuCl2(DMSO)(N, P,N)] 1,fac-[RuCl2(PPh3) (N,P,N)] 2, [RuCl(eta(6)-C6H6)(N, P, N)][O3SCF3] 3 and [Ru(eta(6)-C6H6)(N,P,N)][O3SCF3](2) 4. When tridentate, as in 1, 2, and 4, this ligand co-ordinates in a facial-type mode. In complex 3, it acts as a P,N-chelate with a dangling oxazoline ring. The structures of the ligand, 2 . CH2Cl2. 0.25C(6)H(14) and 3 have been determined by X-ray diffraction. Complexes 1-4 catalyse the transfer hydrogenation reaction between propan-2-ol and ketones. Only small differences in reactivity were observed between 3 and 4, despite the different ligand bonding mode in these complexes. For the best catalyst, 2, yields up to 97% were obtained and turnover frequencies may be as high as 112 000 h(-1).

URL<Go to ISI>://000079052300014