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| | (S)-(-)-5,5'-Bis(diphenylphosphino)-4,4'-bi-1,3-benzodioxole,min.98%(S)-SEGPHOS Basic information | | Reaction |
| Product Name: | (S)-(-)-5,5'-Bis(diphenylphosphino)-4,4'-bi-1,3-benzodioxole,min.98%(S)-SEGPHOS | | Synonyms: | (S)-(-)-5,5'-Bis(diphenylphosphino)-4,4'-bi-1,3-benzodioxole,min.98%(S)-SEGPHOS;Phosphine,1,1'-[(4S)-[4,4'-bi-1,3-benzodioxole]-5,5'-diyl]bis[1,1-diphenyl-;(S)-5,5'-Bis(diphenylphosphino)-4,4'-bibenzodioxole;(S)-SEGPHOS(R);(S)-(-)-5,5'-Bis(diphenylphosphino)-4,4'-bi-1,3-benzodioxole,(S)-(-)-SEGPHOS;(S)-(-)-5,5'-Bis(diphenylphosphino)-4,4'-bi-1,3-benzodioxole,98%;-bi-1,3-benzodioxole,(S)-(-)-SEGPHOS;(S)-(-)-SEGPHOS(regR) | | CAS: | 210169-54-3 | | MF: | C38H28O4P2 | | MW: | 610.57 | | EINECS: | | | Product Categories: | Chiral Phosphine;Segphos Series | | Mol File: | 210169-54-3.mol |  |
| | (S)-(-)-5,5'-Bis(diphenylphosphino)-4,4'-bi-1,3-benzodioxole,min.98%(S)-SEGPHOS Chemical Properties |
| 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 |
| WGK Germany | 3 | | HS Code | 2932.99.7000 |
| | (S)-(-)-5,5'-Bis(diphenylphosphino)-4,4'-bi-1,3-benzodioxole,min.98%(S)-SEGPHOS Usage And Synthesis |
| 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.
| | 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. |
| | (S)-(-)-5,5'-Bis(diphenylphosphino)-4,4'-bi-1,3-benzodioxole,min.98%(S)-SEGPHOS Preparation Products And Raw materials |
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