Highly enantioselective Pd-catalyzed synthesis of P-stereogenic supramolecular phosphines, self-assembly, and implication

TitleHighly enantioselective Pd-catalyzed synthesis of P-stereogenic supramolecular phosphines, self-assembly, and implication
Publication TypeJournal Article
Year of Publication2015
AuthorsKoshti, VS, Mote, NR, Gonnade, RG, Chikkali, SH
JournalOrganometallics
Volume34
Issue20
Pagination4802-4805
Date PublishedOCT
ISSN0276-7333
Abstract

Metal-catalyzed asymmetric addition of a secondary phosphine to an aryl halide is one of the most efficient and reliable approaches for the construction of enantiopure carbon phosphorus bonds. An isolated Pd(II) complex (5) catalyzes the carbon phosphorus coupling reaction between tolylphenylphosphine (la) and 3-iodophenylurea (2b), which proceeds with an unprecedented enantiomeric excess (ee) of 97%. The generality of the strategy has been demonstrated by preparing a small library of a new class of P-stereogenic phosphines with an in-built hydrogen bonding motif for the first time. The P-stereogenic phosphines self-assemble on a metal template via deliberately installed hydrogen-bonding motifs and mimic the bidentate ligand coordination. Interestingly, when it was employed in asymmetric hydrogenation, the supramolecular phosphine {1-(3-(phenyl(o-toly)phosphanyl)pheny)ureal} (6b) produced the corresponding hydrogenated product with the highest enantiomeric excess of 99% along with excellent conversion, demonstrating the potential of these enantioenriched P-chirogenic supramolecular phosphines in asymmetric catalysis.

DOI10.1021/acs.organomet.5b00664
Type of Journal (Indian or Foreign)

Foreign

Impact Factor (IF)

4.186

Divison category: 
Center for Material Characterization (CMC)
Polymer Science & Engineering