| Identification | Back Directory | [Name]
(S)-(-)-5,5'-Bis(diphenylphosphino)-4,4'-bi-1,3-benzodioxole,min.98%(S)-SEGPHOS | [CAS]
210169-54-3 | [Synonyms]
(S)-SEGPHOS(R)
(S)-(-)-SEGPHOS
(S)-(-)-5,5'
(S)-SEGPHOS(R) >=94%
(S)-(-)-SEGPHOS(regR)
(S)-SEGPHOS®
-Bis(diphenylphosphino)-4,4'
-bi-1,3-benzodioxole,(S)-(-)-SEGPHOS
(S)-5,5'-Bis(diphenylphosphino)-4,4'-bibenzodioxole
(S)-(-)-5,5'-Bis(diphenylphosphino)-4,4'-bi-1,3-benzodioxole,98%
(S)-(-)-5,5'-Bis(diphenylphosphino)-4,4'-bi-1,3-benzodioxole, min. 98%
Phosphine,1,1'-[(4S)-[4,4'-bi-1,3-benzodioxole]-5,5'-diyl]bis[1,1-diphenyl-
(S)-(-)-5,5'-Bis(diphenylphosphino)-4,4'-bi-1,3-benzodioxole,(S)-(-)-SEGPHOS
(S)-(-)-5,5'-Bis(diphenylphosphino)-4,4'-bi-1,3-benzodioxole,min.98%(S)-SEGPHOS
(S)-(-)-5,5'-Bis(diphenylphosphino)-4,4'-bi-1,3-benzodioxole, min. 98% (S)-(-)-SEGPHOS(R) | [Molecular Formula]
C38H28O4P2 | [MDL Number]
MFCD09753005 | [MOL File]
210169-54-3.mol | [Molecular Weight]
610.583 |
| Chemical Properties | Back Directory | [Melting point ]
231-235 °C | [Boiling point ]
715.4±60.0 °C(Predicted) | [storage temp. ]
Inert atmosphere,Room Temperature | [form ]
Powder | [color ]
off-white | [optical activity]
[α]20/D -11°, c = 0.5 in chloroform | [InChIKey]
RZZDRSHFIVOQAF-UHFFFAOYSA-N |
| Questions And Answer | Back Directory | [Reaction]
- Biaryl bisphosphine ligand with narrow dihedral angle. The SEGPHOS® ligand has been applied to a variety of metal catalyzed reactions. In many cases, yields and enantioselectivities, exceed results obtained earlier using BINAP.
- As ruthenium complex, SEGPHOS® generally gives higher levels of chiral induction in asymmetric hydrogenations of α,β,and γ-functionalized ketones. See ruthenium complexes 44-0096, 44-0518, 44-0168.
- Used in Rh-catalyzed transformations such as: (a) 1,4-addition of boronic acids to coumarins,4 (b) addition of titanium reagents to imines, (c) cotrimerization of alkenes and acetylenes, (d) double [2+2+2] cycloaddition,11 (e) indanone formation.12a,b
- Used in Pd-catalyzed transformations such as: (a) cycloaddition of 1,6-enyne, (b) arylative cyclization of allenyl aldehydes with boronic acids,13 (c) synthesis of chromans.
- Used in Cu-catalyzed transformations such as: (a) nitroso Diels-Alder, (b) reductive aldol condensation, (c) conjugate reduction of unsaturated sulfones,15 and phophonates.
- Iridium-catalyzed asymmetric hydrogenation of quinolines activated by chloroformates.
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| Hazard Information | Back Directory | [Uses]
(S)-(-)-SEGPHOS? is a chelating ligand used to prepare coordination complex catalysts, such as its use in Pd catalysts for the enantioselective synthesis of spiro- or benzofused hetereocycles with exocyclic olefins via enantioselective intramolecular dearomative Heck reaction of indoles, benzofurans, pyrroles and furans. |
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