Base-mediated 1, 6-conjugate addition of the Seyferth–Gilbert reagent to para-quinone methides. Issue 25 (7th June 2018)

• Record Type: Journal Article
• Authors: Gupta, Ashis Kumar; Ahamad, Shakir; Vaishanv, Narendra Kumar; Kant, Ruchir; Mohanan, Kishor
• Is Part Of: Organic & biomolecular chemistry. Volume 16:Issue 25(2018)
• Page Start: 4623
• Page End: 4627
• Publication Date: 2018-06-07
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c8ob01017j
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : An efficient 1, 6-conjugate addition reaction of the Seyferth–Gilbert reagent (SGR) to p -quinone methides leading to the synthesis of diarylmethylated diazomethylphosphonates is reported. 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.