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| Product Name: | (R)-SEGPHOS | | Synonyms: | (R)-(+)-5,5'-Bis(diphenylphosphino)-4,4'-bi-1,3-benzodioxole,min.98%(R)-SEGPHOS;(R)-(+)-5,5μ-Bis(diphenylphosphino)-4,4μ-bi-1,3-benzodioxole, [4(R)-(4,4μ-bi-1,3-benzodioxole)-5,5μ-diyl]bis[diphenylphosphine];(R)-SEGPHOS(R);(R)-(+)-SEGPHOS;Phosphine,1,1'-[(4R)-[4,4'-bi-1,3-benzodioxole]-5,5'-diyl]bis[1,1-diphenyl-;(R)-(+)-5,5'-Bis(diphenylphosphino)-4,4'-bi-1,3-benzodioxole,(R)-(+)-SEGPHOS;(R)-(+)-5,5'-Bis(diphenylphosphino)-4,4'-bi-1,3-benzodioxole;[(4R)-[4,4'-Bi-1,3-benzodioxole]-5,5'-diyl]bis[diphenylphosphine] | | CAS: | 244261-66-3 | | MF: | C38H28O4P2 | | MW: | 610.59 | | EINECS: | | | Product Categories: | Chiral Phosphine;Segphos Series | | Mol File: | 244261-66-3.mol |  |
| | (R)-SEGPHOS Chemical Properties |
| Melting point | 168-172 °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 |
| WGK Germany | 3 | | HS Code | 2932.99.7000 |
| | (R)-SEGPHOS Usage And Synthesis |
| Reactions |
- 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.
- Used in Rh-catalyzed transformations such as: (a) 1,4-addition of boronic acids to coumarins, (b) addition of titanium reagents to imines,(c) cotrimerization of alkenes and acetylenes,10 (d)double [2+2+2] cycloaddition,11 (e) indanone formation.
- 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,and phophonates.
- Iridium-catalyzed asymmetric hydrogenation of quinolines activated by chloroformates.
- Iridium-catalyzed asymmetric transfer hydrogenation used in polyketide construction.
- Rhodium-catalyzed asymmetric hydroarylation of 3-pyrrolines.
- Palladium-catalyzed regio- and enantioselective dearomatization.
| | Uses | (R)-(+)-SEGPHOS? is a chelating ligand used to prepare coordination complex catalysts, such as its use in Pd catalysts for the enantioselective addition of diesters to 3,3-difluoropropenes, and in the Ni-based catalyst for the asymmetric propargylic amination of propargylic carbonates with an internal alkyne group. |
| | (R)-SEGPHOS Preparation Products And Raw materials |
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