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.
Laboratory of Organic and Medicinal Chemistry, National Institute of Chemistry, Hajdrihova 19, SI-1001 Ljubljana, Slovenia.
Borut
B
Zupancic
Barbara
B
Mohar
Michel
M
Stephan
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