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The Tetraethylphosphorodiamidate (OP(O)(NEt2)2) Directed Metalation Group (DMG). Directed ortho and Lateral Metalation and the Phospha Anionic Fries Rearrangement

Manlio Alessi, Jignesh J. Patel, Kristina Zumbansen and Victor Snieckus*

*Department of Chemistry, Queen’s University, 90 Bader Lane, Kingston K7L 3N6, ON Canada, Email: snieckuschem.queensu.ca

M. Alessi, J. J. Patel, K. Zumbansen, V. Snieckus, Org. Lett., 2020, 22, 2147-2151.

DOI: 10.1021/acs.orglett.0c00094 (free Supporting Information)


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Abstract

The tetraethylphosphorodiamidate (OP(O)(NEt2)2) group is an effective directed metalation group (DMG), which enables a general synthesis of ortho-substituted aryl and naphthyl phosphorodiamidates. The directing power of the OP(O)(NEt2)2 group is comparable to that of the OCONEt2 group.

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Key Words

directed ortho metalation


ID: J54-Y2020