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A substituent-tolerant synthetic approach to N/P-“loaded” heteroarenes

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Abstract

Tetrazines react with OCP−1 through a reverse electron demand Diels–Alder process to produce 3,6-disubstituted-1,2,4-diazaphosphinin-5-olates. DFT calculations reveal that both Diels–Alder and subsequent aromatization barriers are low for both EWG and ED tetrazine substituents. The structure of the solid sodium salt shows the interaction of Na+ with aryloxide and also both nitrogens of a neighboring anion, leading to coordination polymer character. 1,2,4-Diazaphosphinin-5-olates react as nucleophiles towards MeI and R3SiCl, respectively, and were installed on the (Ph3P)2Ru(CO)H fragment to investigate their properties as ligands.

Graphical abstract: A substituent-tolerant synthetic approach to N/P-“loaded” heteroarenes

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Publication details

The article was received on 08 Feb 2018, accepted on 15 Mar 2018 and first published on 16 Mar 2018


Article type: Communication
DOI: 10.1039/C8DT00533H
Citation: Dalton Trans., 2018, Advance Article
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    A substituent-tolerant synthetic approach to N/P-“loaded” heteroarenes

    A. V. Polezhaev, D. M. Beagan, A. C. Cabelof, C. Chen and K. G. Caulton, Dalton Trans., 2018, Advance Article , DOI: 10.1039/C8DT00533H

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