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Metal-catalyzed aziridination of alkenes by organic azides: a mechanistic DFT investigation

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Abstract

The DFT B3LYP/6–31G(d,p) approach is used to study alkene aziridination by azides through catalyzed routes involving a metal nitrenoid intermediate. The catalysts studied are copper(II) triflate, cobalt(II) porphin, and ruthenium(II) porphin. Three azides RN3 (R = H, Me, and Ac) react with alkene substrates in the presence of these catalysts leading to aziridine formation by a two-step catalyzed mechanism. The azide reacts with the catalyst in Step I to first form a metal nitrenoid via transition state TS1. The Ru(porph) catalyst is particularly effective for Step I. Then, the metal nitrenoid adds to alkene through Step II via TS2 giving the aziridine, the metal catalyst, and N2. Cu(trfl)2 is most effective as a catalyst for Step II. The facility order H > Me > Ac (with respect to the azide R group) holds for Step I and the reverse order for Step II. MP2 results on some select minima for Step II largely reproduce the DFT trends. Transition states TS1 and TS2 are characterized as being “early” or “late” in good accord with the Hammond postulate.

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S.P.D. thanks the University Grants Commission, Government of India, New Delhi, for financial assistance through the UGC Research Fellowship for Meritorious Students (Award No. F. 5-119/2007(BSR).

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  1. Department of Chemistry, North-Eastern Hill University, Shillong, 793022, India

    Shougaijam Premila Devi & R. H. Duncan Lyngdoh

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Devi, S.P., Lyngdoh, R.H.D. Metal-catalyzed aziridination of alkenes by organic azides: a mechanistic DFT investigation. Struct Chem 32, 1431–1449 (2021). https://doi.org/10.1007/s11224-020-01720-8

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