Kelliphite

Kelliphite is an acronym for the organophosphorus compound 6,6'-[(1,1'-Biphenyl-2,2'-diyl)bis(oxy)]bis[4,8-di-tbutyl-1,2,10,11-tetramethyl]dibenzo[d,f][1,3,2]dioxaphosphepin. This chiral ligand is widely used in asymmetric synthesis.[1][2] In one example, this ligand is used to form a rhodium complex to catalyze asymmetric hydroformylation of prochiral olefins. It has been shown that high substrate concentrations as well as a wide variety of functional groups are tolerated. [3]

Kelliphite
Skeletal formula of kelliphite
Ball-and-stick model of the kelliphite molecule
Names
Preferred IUPAC name
6,6′-{[1,1′-Biphenyl]-2,2′-diylbis(oxy)}bis(4,8-di-tert-butyl-1,2,10,11-tetramethyl-6H-dibenzo[d,f][1,3,2]dioxaphosphepine)
Other names
Kelliphite
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C60H72O6P2/c1-33-29-43(57(9,10)11)53-49(37(33)5)50-38(6)34(2)30-44(58(12,13)14)54(50)64-67(63-53)61-47-27-23-21-25-41(47)42-26-22-24-28-48(42)62-68-65-55-45(59(15,16)17)31-35(3)39(7)51(55)52-40(8)36(4)32-46(56(52)66-68)60(18,19)20/h21-32H,1-20H3
    Key: BWNYBZZRRYVGQK-UHFFFAOYSA-N
  • CC1=CC(=C2C(=C1C)C3=C(C(=CC(=C3OP(O2)OC4=CC=CC=C4C5=CC=CC=C5OP6OC7=C(C=C(C(=C7C8=C(C(=CC(=C8O6)C(C)(C)C)C)C)C)C)C(C)(C)C)C(C)(C)C)C)C)C(C)(C)C
Properties
C60H72O6P2
Molar mass 951.178 g·mol−1
organic solvents
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

References
  1. Clark, Thomas P.; Landis, CR; Freed, SL; Klosin, J; Abboud, KA (2005). "Highly Active, Regioselective, and Enantioselective Hydroformylation with Rh Catalysts Ligated by Bis-3,4-diazaphospholanes". J. Am. Chem. Soc. 127 (14): 5040–2. CiteSeerX 10.1.1.601.7762. doi:10.1021/ja050148o. PMID 15810837.
  2. Cobley, Christopher J.; Gardner, K; Klosin, J; Praquin, C; Hill, C; Whiteker, GT; Zanotti-Gerosa, A; Petersen, JL; Abboud, KA (2004). "Synthesis and Application of a New Bisphosphite Ligand Collection for Asymmetric Hydroformylation of Allyl Cyanide". J. Org. Chem. 69 (12): 4031–40. doi:10.1021/jo040128p. PMID 15176828.
  3. Cobley, Christopher J.; Klosin, Jerzy; Qin, Cheng; Whiteker, Gregory T. (2004). "Parallel Ligand Screening on Olefin Mixtures in Asymmetric Hydroformylation Reactions". Org. Lett. 6 (19): 3277–80. doi:10.1021/ol0487938. PMID 15355031.
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