A Dicopper Nitrenoid by Oxidation of a Cu'Cu' Core: Synthesis, Electronic Structure, and Reactivity

Desnoyer, Addison N.; Nicolay, Amélie; Ziegler, Micah S.; Lakshmi, K. V.; Cundari, Thomas R.; Tilley, T. Don

doi:10.1021/jacs.1c02235

A Dicopper Nitrenoid by Oxidation of a Cu'Cu' Core: Synthesis, Electronic Structure, and Reactivity

Journal Article · Tue Apr 20 00:00:00 EDT 2021 · Journal of the American Chemical Society

DOI:https://doi.org/10.1021/jacs.1c02235· OSTI ID:1831110

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Univ. of California, Berkeley, CA (United States); Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States); UNT
Univ. of California, Berkeley, CA (United States); Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States)
Rensselaer Polytechnic Inst., Troy, NY (United States)
Univ. of North Texas, Denton, TX (United States)

A dicopper nitrenoid complex was prepared by formal oxidative addition of the nitrenoid fragment to a dicopper(I) center by reaction with the iminoiodinane PhINTs (Ts = tosylate). This nitrenoid complex, (DPFN)Cu₂(μ-NTs)[NTf₂]₂ (DPFN = 2,7-bis(fluorodi(2-pyridyl)methyl)-1,8-naphthyridine), is a powerful H atom abstractor that reacts with a range of strong C–H bonds to form a mixed-valence Cu(I)/Cu(II) μ-NHTs amido complex in the first example of a clean H atom transfer to a dicopper nitrenoid core. In line with this reactivity, DFT calculations reveal that the nitrenoid is best described as an iminyl (NR radical anion) complex. The nitrenoid was trapped by the addition of water to form a mixed-donor hydroxo/amido dicopper(II) complex, which was independently obtained by reaction of a Cu₂(μ-OH)₂ complex with an amine through a protonolysis pathway. Furthermore, this mixed-donor complex is an analogue for the proposed intermediate in copper-catalyzed Chan–Evans–Lam coupling, which proceeds via C–X (X = N or O) bond formation. Treatment of the dicopper(II) mixed donor complex with MgPh₂(THF)₂ resulted in generation of a mixture that includes both phenol and a previously reported dicopper(I) bridging phenyl complex, illustrating that both reduction of dicopper(II) to dicopper(I) and concomitant C–X bond formation are feasible.

View Accepted Manuscript (DOE)

Research Organization:: Univ. of North Texas, Denton, TX (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES). Chemical Sciences, Geosciences & Biosciences Division

Grant/Contract Number:: AC02-05CH11231; FG02-03ER15387

OSTI ID:: 1831110

Journal Information:: Journal of the American Chemical Society, Journal Name: Journal of the American Chemical Society Journal Issue: 18 Vol. 143; ISSN 0002-7863

Publisher:: American Chemical Society (ACS)Copyright Statement

Country of Publication:: United States

Language:: English

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A Dicopper Nitrenoid by Oxidation of a Cu'Cu' Core: Synthesis, Electronic Structure, and Reactivity

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