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Issue 25, 2018
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Base-mediated 1,6-conjugate addition of the Seyferth–Gilbert reagent to para-quinone methides

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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.

Graphical abstract: Base-mediated 1,6-conjugate addition of the Seyferth–Gilbert reagent to para-quinone methides

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Publication details

The article was received on 02 May 2018, accepted on 29 May 2018 and first published on 30 May 2018


Article type: Communication
DOI: 10.1039/C8OB01017J
Citation: Org. Biomol. Chem., 2018,16, 4623-4627
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    Base-mediated 1,6-conjugate addition of the Seyferth–Gilbert reagent to para-quinone methides

    A. K. Gupta, S. Ahamad, N. K. Vaishanv, R. Kant and K. Mohanan, Org. Biomol. Chem., 2018, 16, 4623
    DOI: 10.1039/C8OB01017J

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