Traditional radical-catalyzed methods to prepare alkylphosphines are not suitable for the target molecule, tricyclohexylphosphine, otherwise known as CYTOP® 366. Through computational study, we explore why this tertiary phosphine is inaccessible via a radical-catalyzed addition and describe an alternative pathway to our target, which not only achieves good yield and purity but is also a safe and workable route for industrial scale manufacture.

Abstract

Homogenous catalysis is an essential tool within the commercial manufacture of bulk and fine chemicals. Within this, phosphine ligands, such as tricyclohexylphosphine, otherwise known as CYTOP® 366, are a crucial component. When designing a pathway to your ligand of choice, some key considerations include safety, yield and quality, but at commercial volumes we must also balance cost and consider the technologies readily available. Herein, we report the synthetic route that was chosen to manufacture tricyclohexylphosphine at commercial scale. We also consider, with the use of computational calculations, why traditional hydrophosphination methods failed, where the selected pathway succeeded.