An efficient P-arylation of secondary phosphine oxides has been achieved through the ligand-free copper-catalyzed addition of H–P(O) bonds to in situ generated arynes at room temperature. This transformation provides a straightforward route to the formation of the aryl–P bond with wide functional group compatibility, which produces arylphosphine oxides in up to 99% yield.
An efficient method was developed for the synthesis of a variety of arylphosphorus compounds from P–H compounds using o-(trimethylsilyl)aryl triflates as aryne precursors. The reaction provides a practical preparation of various arylphosphorus compounds via aryne intermediates utilizing diarylphosphine oxides and dialkyl phosphites as the nucleophiles.
Disclosed are novel naphthalocyanine compounds which strongly absorb light of the near infrared region and which are chemically stable and highly soluble to an organic solvent. The naphthalocyanine compounds are represented by the following formula [1];
wherein X represents
( wherein R¹ and R² respectively represent a hydroxyl group, an alkyl group, an aryl group or an alkoxy group ) and M represents 2H, a metal atom, a metal oxide residue or a metal chloride residue. The present invention also provides a process for producing the naphthalocyanine compounds, intermediates thereof and a process for producing the intermediates.
The novel P-arylation of dialkyl phosphites and secondary phosphine oxides with arynes has been achieved. The reactions produce dialkyl arylphosphonates in 71-99% yield and tertiary phosphine oxides in 68-92% yield under mild conditions.