(R)-(+)-XylBINAP
PRICE INQUIRYCatalog Number
ACM137219864-4
Product Name
(R)-(+)-XylBINAP
Structure
![{[CurrentData.Name]}](https://resource.alfachemic.com/structure/137219-86-4.gif)
CAS
137219-86-4
IUPAC Name
[1-[2-bis(3,5-dimethylphenyl)phosphanylnaphthalen-1-yl]naphthalen-2-yl]-bis(3,5-dimethylphenyl)phosphane;
Molecular Weight
734.904g/mol
Molecular Formula
C52H48P2;
Canonical SMILES
CC1=CC(=CC(=C1)P(C2=C(C3=CC=CC=C3C=C2)C4=C(C=CC5=CC=CC=C54)P(C6=CC(=CC(=C6)C)C)C7=CC(=CC(=C7)C)C)C8=CC(=CC(=C8)C)C)C;
InChI
InChI=1S/C52H48P2/c1-33-21-34(2)26-43(25-33)53(44-27-35(3)22-36(4)28-44)49-19-17-41-13-9-11-15-47(41)51(49)52-48-16-12-10-14-42(48)18-20-50(52)54(45-29-37(5)23-38(6)30-45)46-31-39(7)24-40(8)32-46/h9-32H,1-8H3;
InChI Key
MXGXXBYVDMVJAO-UHFFFAOYSA-N;
Complexity
999
Covalently-Bonded Unit Count
1
Exact Mass
734.323g/mol
Heavy Atom Count
54
Monoisotopic Mass
734.323g/mol
Rotatable Bond Count
7
Topological Polar Surface Area
0A^2
Application
(R)-(+)-XylBINAP serves a critical role as a phosphine-based ligand in the formulation of a diverse array of catalysts. It is utilized in the development of palladium catalysts for asymmetric dearomative alkenylation of indoles through reductive-Heck reactions. This versatile ligand is also employed in copper-catalyzed asymmetric Mannich-type reactions involving N-acylimino esters, as well as in the enantioselective fluorination of oxindoles. Additionally, (R)-(+)-XylBINAP facilitates [2+2+2] cycloaddition of tetraynes and hexaynes, and is instrumental in the asymmetric reduction of ketones via ruthenium-catalyzed transfer hydrogenation. Furthermore, it aids in the asymmetric hydroboration of unsaturated imines, making it an essential component in the field of asymmetric synthesis.
April 23, 2025
Invaluable Ligand for Asymmetric Reactions
(R)-(+)-XylBINAP has significantly enhanced our research in enantioselective fluorination of oxindoles. Its efficiency in catalysis and reliability in asymmetric reduction processes have been remarkable. A must-have for industrial applications in asymmetric synthesis.
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