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Issue 19, 2020
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Facile addition of E–H bonds to a dicarbondiphosphide

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Charge transfer at P atoms in an N-heterocyclic carbene stabilized 6π-electron aromatic dicarbondiphosphide 1 has been observed upon interaction with a variety of small molecule substrates that feature a polar E–H bond (E = C, N, and O). As a result, these P atoms exhibit fleeting nucleophilicity and electrophilicity behaving as potential independent active sites, which effect the spontaneous addition of E–H bonds leading to a series of unsymmetrical 1,3-diphosphetane frameworks bearing P–C (2), P–N (6 and 7), and P–O bonds (8b, 8c, and 9). In addition, 1,3-diphosphetanium salts have been achieved when X-type substituents are weakly coordinating (i.e. [(CN)2CH] (3), I (4), and [(PhOH)2PhO] (10)). The mechanisms of such transformations are investigated using density functional theory calculations.

Graphical abstract: Facile addition of E–H bonds to a dicarbondiphosphide

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Supplementary files

Article information

12 Apr 2020
20 Apr 2020
First published
21 Apr 2020

Dalton Trans., 2020,49, 6384-6390
Article type

Facile addition of E–H bonds to a dicarbondiphosphide

X. Zhang, X. Chen, H. Zhai, S. Liu, C. Hu, L. L. Liu, S. Wang and Z. Li, Dalton Trans., 2020, 49, 6384
DOI: 10.1039/D0DT01341B

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