1383809-98-0

Basic information

• Product Name: (R)-(2-bromophenyl)-cyclohexylphenylphosphine borane
• CAS NO: 1383809-98-0
• Molecular Weight: 361.069
• Mol File: 1383809-98-0.mol

Chemical Properties

• CAS DataBase Reference: (R)-(2-bromophenyl)-cyclohexylphenylphosphine borane(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(2-bromophenyl)-cyclohexylphenylphosphine borane(1383809-98-0)
• EPA Substance Registry System: (R)-(2-bromophenyl)-cyclohexylphenylphosphine borane(1383809-98-0)

Safety Data

• Hazardous Substances Data: 1383809-98-0(Hazardous Substances Data)

Upstream product

• 1383810-05-6 C₁₂H₂₀BP 
• 583-53-9 2,3-dibromobenzene 
• 1383810-05-6 (R)-cyclohexylphenylphosphine borane 

Relevant articles and documents

Efficient Stereoselective Synthesis of o -Functionalized P-Chirogenic Phosphines Applied to Asymmetric Catalysis

The stereoselective synthesis of P-chirogenic o-halogenophenylphosphines and their use for the preparation of o-functionalized derivatives are reported. The key step of this synthesis is based on the reaction of a P-chirogenic secondary phosphine borane,

P-CHIROGENIC ORGANOPHOSPHORUS COMPOUNDS

The present invention relates to novel P-chirogenic organophosphorus compounds of general formula (I). The present invention also provides a process for the synthesis of said compounds of formula (I). The present invention also relates to intermediate products of general formulae (II), (III) and (IV), as shown below, which are involved in the synthesis of compounds (I). Further, the invention relates to metal complexes comprising compounds (I) as ligands. The novel compounds and complexes of the present invention are useful in asymmetric catalysis by transition metal complexes or organocatalysis, especially for asymmetric hydrogenation or allylation. Compounds of general formula (I) may useful as agrochemical and therapeutic substances, or as reagents or intermediates for fine chemistry.

Stereoselective synthesis of o-bromo (or iodo)aryl P-chirogenic phosphines based on aryne chemistry

The efficient synthesis of chiral or achiral tertiary phosphines bearing an o-bromo (or iodo)aryl substituent is described. The key step of this synthesis is based on the reaction of a secondary phosphine borane with the 1,2-dibromo (or diiodo)arene, owing to the formation in situ of an aryne species in the presence of n-butyllithium. When P-chirogenic secondary phosphine boranes were used, the corresponding o-halogeno-arylphosphine boranes were obtained without racemization in moderate to good yields and with ee up to 99%. The stereochemistry of the reaction, with complete retention of the configuration at the P atom, has been established by X-ray structures of P-chirogenic o-halogenophenyl phosphine borane complexes. The decomplexation of the borane was easily achieved without racemization using DABCO to obtain the free o-halogeno-arylphosphines in high yields.