Base-mediated 1,6-conjugate addition of the Seyferth–Gilbert reagent to para-quinone methides?
Organic & Biomolecular Chemistry Pub Date: 2018-05-30 DOI: 10.1039/C8OB01017J
Abstract
A 1,6-conjugate addition reaction of the Seyferth–Gilbert reagent (SGR) to p-quinone methides is reported. This base-mediated protocol allows rapid access to diarylmethylated diazomethylphosphonates. The reaction proceeds under mild basic conditions, making it a practical approach for the synthesis of diarylmethylated diazomethylphosphonates with a broad substrate scope. Interestingly, the treatment of the conjugate adduct with a catalytic amount of rhodium acetate resulted in the 1,2-aryl migration of the rhodium carbenoid intermediate to generate the corresponding 1,2-diaryl alkenylphosphonates in excellent yields.
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Journal Name：Organic & Biomolecular Chemistry
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CAS no.: 89640-58-4
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