Photoactivation of Hydrazones for the Synthesis of Diarylalkanes and Trialkylmethylboronates: The Key Role Played by Soluble Base.

ABSTRACT

The synthesis of diaryl alkanes and tertiary organoboronates via Barluenga coupling at room temperature occurred via photoactivated conversion of aryl sulfonyl hydrazones to diazo compounds in the presence of soluble bases. The combination of arylsulfonyl hydrazone and a soluble base is necessary to provide a near-UV chromophore. Using aromatic hydrazones and aromatic boronic acids resulted in rapid deboronation because of the instability of dibenzylic boron intermediates. Alkyl hydrazones allowed the isolation of derivatives of the tertiary boronate.