Impact on hydrogenation catalytic cycle of the R groups' cyclic feature in "R-SMS-Phos".
A series of R-SMS-Phos ligands was evaluated in the Rh(I)-catalyzed hydrogenation of a set of olefins showing a marked influence of the cyclic nature and structure of the R groups. Overall, cPen- and Cy-SMS-Phos performed efficiently, while Ph- and Bn-SMS-Phos exhibited slower kinetics and furnished lower ee's also compared with C(6)F(5)CH(2)-SMS-Phos. The Rh(I)-(Cy-SMS-Phos) catalyst was screened under mild conditions displaying excellent enantioselectivities and high TOFs. Cases of catalysis under catalyst or substrate control were identified.
Zupancic
Borut
B
Laboratory of Organic and Medicinal Chemistry, National Institute of Chemistry, Hajdrihova 19, SI-1001 Ljubljana, Slovenia.
Mohar
Barbara
B
Stephan
Michel
M
D000475:Alkenes / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D006865:Hydrogenation; D007700:Kinetics; D008024:Ligands; D008968:Molecular Conformation; D009942:Organometallic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D012238:Rhodium / Q000737:chemistry*; D013237:Stereoisomerism
D000475:Alkenes; D008024:Ligands; D009942:Organometallic Compounds; D012238:Rhodium