Base-mediated 1,6-conjugate addition of the Seyferth-Gilbert reagent to para-quinone methides.

Org Biomol Chem

Medicinal and Process Chemistry Division, CSIR-Central Drug Research Institute, Lucknow 226031, India. and Molecular and Structural Biology Division, CSIR-Central Drug Research Institute, Lucknow 226031, India.

Published: July 2018


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Article 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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http://dx.doi.org/10.1039/c8ob01017jDOI Listing

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