Synthesis and Structure of Sterically Crowded Triarylphosphine Bearing 4-Bromo-2,6-Bis(4-tert-Butylphenyl)Phenyl Group

Abstract

A novel sterically crowded triarylphosphine bearing a 2,6-diaryl-4-bromophenyl group, [4-bromo-2,6-bis(4-tert-butylphenyl)phenyl]bis(2,4,6-triisopropylphenyl)phosphine (1), was synthesized. The X-ray crystallography revealed that the bond angles and lengths around the phosphorus atom (110.9°, 1.846 Å) are comparable to those of tris(2,4,6-triisopropylphenyl)phosphine and its derivatives. Triarylphosphine 1 is reversibly oxidized to the radical cation at the potential close to that of the typical sterically crowded (bromoaryl)phosphine, (4-bromo-2,6-diisopropylphenyl)bis(2,4,6-triisopropylphenyl)phosphine, and exhibits the UV absorption at long wavelength (λ_max 332 nm) characteristic of the sterically crowded triarylphosphines. Thus, triarylphosphine 1 can be regarded to be a promising candidate for the key synthetic intermediate or building block to the functional molecules bearing sterically crowded triarylphosphine moieties.

GRAPHICAL ABSTRACT

Keywords:

• Triarylphosphine
• bromo group
• X-ray crystallography
• oxidation potential
• UV-Vis spectrum

Additional information

Funding

This work was supported by JSPS KAKENHI Grant numbers 15550025, 17310063 and 25600020.