952023-91-5

Basic information

• Product Name: [(S,S)-2,3-bis(tert-butylmethylphosphino)quinoxaline]palladium(II)dichloride
• Synonyms: [(S,S)-2,3-bis(tert-butylmethylphosphino)quinoxaline]palladium(II)dichloride
• CAS NO: 952023-91-5
• Molecular Weight: 511.707
• Mol File: 952023-91-5.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: [(S,S)-2,3-bis(tert-butylmethylphosphino)quinoxaline]palladium(II)dichloride(CAS DataBase Reference)
• NIST Chemistry Reference: [(S,S)-2,3-bis(tert-butylmethylphosphino)quinoxaline]palladium(II)dichloride(952023-91-5)
• EPA Substance Registry System: [(S,S)-2,3-bis(tert-butylmethylphosphino)quinoxaline]palladium(II)dichloride(952023-91-5)

Safety Data

• Hazardous Substances Data: 952023-91-5(Hazardous Substances Data)

Upstream product

• 1107608-80-9 (R,R)-(-)-2,3-bis(tert-butylmethylphosphino)qinoxaline 
• 15617-18-2 bis(benzonitrile)palladium(II) dichloride 
• 1107608-80-9 2,3-bis[(S)-(1,1-dimethylethyl)methylphosphino]quinoxaline 

Relevant articles and documents

Congested C-C bonds by Pd-catalyzed enantioselective allyl-allyl cross-coupling, a mechanism-guided solution

Under the influence of a chiral bidentate diphosphine ligand, the Pd-catalyzed asymmetric cross-coupling of allylboron reagents and allylic electrophiles establishes 1,5-dienes with adjacent stereocenters in high regio-and stereoselectivity. A mechanistic study of the coupling utilizing reaction calorimetry and density functional theory analysis suggests that the reaction operates through an inner-sphere 3,3′-reductive elimination pathway, which is both rate-defining and stereodefining. Coupled with optimized reaction conditions, this mechanistic detail is used to expand the scope of allyl-allyl couplings to allow the generation of 1,5-dienes with tertiary centers adjacent to quaternary centers as well as a unique set of cyclic structures.