CAS 135139-00-3 (S)-(-)-XylBINAP - Catalysts / Alfa Chemistry

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

Exact Mass

734.323g/mol

Heavy Atom Count

Monoisotopic Mass

734.323g/mol

Rotatable Bond Count

Topological Polar Surface Area

0A^2

Application

(S)-(-)-XylBINAP serves as a versatile and highly efficient catalyst and ligand in a variety of asymmetric synthesis reactions. It is instrumental in the asymmetric hydrogenation of benzophenone and plays a key role in the regio- and stereoselective preparation of axially chiral arylnaphthalene derivatives through rhodium-catalyzed [2+2+2] cycloaddition of diynes with naphthalenepropynoic acid derivatives. Furthermore, it enables regiodivergent rhodium-catalyzed [(2+2)+2] carbocyclization of 1,6-enynes with methyl propiolates and facilitates ligand-controlled regioselective and stereoselective desymmetrizing rhodium-catalyzed allylic arylation of meso cyclopentene dicarbonates using arylboronic acids to produce regioisomeric arylcyclopentenols. (S)-(-)-XylBINAP also contributes to platinum(II) complex-catalyzed enantioselective aldol reactions with ketene silyl acetals in DMF at ambient temperature, aiding stereoselective N,O-biaryl formation via Rh-catalyzed cycloaddition of ynamides with diynes. It is a vital ligand in copper-catalyzed asymmetric Mannich-type reactions of N-acylimino esters and supports enantioselective fluorination of oxindoles. Additionally, it is used in [2+2+2] cycloaddition of tetraynes and hexaynes as well as in the asymmetric reduction of ketones via ruthenium-catalyzed transfer hydrogenation, and it facilitates the asymmetric hydroboration of unsaturated imines.

January 26, 2025

Excellent Catalyst for Complex Reactions

The (S)-(-)-XylBINAP from Alfa Chemistry greatly enhanced our asymmetric hydrogenation experiments. Its application in rhodium-catalyzed [2+2+2] cycloadditions proved efficient, delivering high stereoselectivity and purity in our laboratory research. Highly recommended!