210169-54-3

Basic information

• 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;(S)-SEGPHOS(R);(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)-(-)-5,5'-Bis(diphenylphosphino)-4,4'-bi-1,3-benzodioxole,(S)-(-)-SEGPHOS;(S)-(-)-SEGPHOS(regR);(S)-SEGPHOS(R) >=94%
• CAS NO: 210169-54-3
• Molecular Formula: C₃₈H₂₈O₄P₂
• Molecular Weight: 610.583
• Product Categories: Chiral Phosphine;Segphos Series
• Mol File: 210169-54-3.mol

Chemical Properties

• Melting Point: 231-235 °C
• Boiling Point: 715.4±60.0 °C(Predicted)
• Appearance: off-white/Powder
• Storage Temp.: Inert atmosphere,Room Temperature
• CAS DataBase Reference: (S)-(-)-5,5'-Bis(diphenylphosphino)-4,4'-bi-1,3-benzodioxole,min.98%(S)-SEGPHOS(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(-)-5,5'-Bis(diphenylphosphino)-4,4'-bi-1,3-benzodioxole,min.98%(S)-SEGPHOS(210169-54-3)
• EPA Substance Registry System: (S)-(-)-5,5'-Bis(diphenylphosphino)-4,4'-bi-1,3-benzodioxole,min.98%(S)-SEGPHOS(210169-54-3)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 210169-54-3(Hazardous Substances Data)

Usage

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.

Downstream Products

• 1208092-27-6 [(S)-(+)-5,5'-bis(diphenylphosphino)-4,4'-bi-1,3-benzodioxole][4-cyano-3-nitrobenzenecarboxylato] [1,2,3-eta-2-propenyl Ir(III)] 
• 1158398-82-3 Ir(allyl)((S)-SEGPHOS)(m-nitrobenzoate(-H)-kappa.C,O) 
• 670256-87-8 [Rh(CO)Cl((C₆H₂OCH₂OP(C₆H₅)2)2)] 
• 1005350-79-7 [((R)-segphos)Ni(C₆H₄-4-CN)(Br)] 

Relevant articles and documents

Ruthenium-I0D0-optically active phosphine complex

This invention is concerned with a ruthenium-iodo-optically active bidentate phosphine complex of the formula (I):[Ru-(I)q-(T1)n(SOL)r(L)]m(T2)p(I)s(I)wherein T1 represents a carboxylic acid anion, SOL represents a polar solvent, L represents an optically active bidentate phosphine ligand, T2 represents an anion different from halogen atom anions and carboxylic acid anions, n denotes 0 or 1, r denotes 0, 3 or 4, m denotes 1 or 2, q denotes 0 or 1, or where m is 2, q may represent 1 or 1.5, p denotes 0 or 1, and s denotes 0, 1 or 2 is prepared. Said phosphine complex is usefull as an efficient catalyst for asymmetrically hydrogenating 4-methylene-2-oxetanone into optically active 4-methyl-2-oxetanone.

Chiral diphosphine compound intermediate for preparing the same transition metal complex having the same diphosphine compound as ligand and asymmetric hydrogenation catalyst

A novel diphosphine compound of the formula (I): STR1 where R1 and R2 represent independently cycloalkyl, unsubstituted or substituted phenyl, or a five-membered heteroaromatic ring. The compound is useful as a ligand for an asymmetric reaction, in particular, as an asymmetric hydrogenation catalyst.