C–H Amination Mediated by Cobalt Organoazide Adducts and the Corresponding Cobalt Nitrenoid Intermediates

Baek, Yunjung; Das, Anuvab; Zheng, Shao-Liang; Reibenspies, Joseph H.; Powers, David C.; Betley, Theodore A.

doi:10.1021/jacs.0c04252

Title: C–H Amination Mediated by Cobalt Organoazide Adducts and the Corresponding Cobalt Nitrenoid Intermediates

Journal Article · Tue May 26 00:00:00 EDT 2020 · Journal of the American Chemical Society

DOI:https://doi.org/10.1021/jacs.0c04252· OSTI ID:1780826

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^[1]; Reibenspies, Joseph H. ^[2];

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Harvard Univ., Cambridge, MA (United States)
Texas A & M Univ., College Station, TX (United States)

Treatment of (^ArL)CoBr (^ArL = 5-mesityl-1,9-(2,4,6-Ph₃C₆H₂)dipyrrin) with a stoichiometric amount of 1-azido-4-(tert-butyl)benzene N₃(C₆H₄-p-^tBu) furnished the corresponding four-coordinate organoazide-bound complex (^ArL)CoBr(N₃(C₆H₄-p-^tBu)). Characterization of the complex by single crystal X-ray diffraction, solution IR spectroscopy, and EPR spectroscopy indicated redox innocent ligation of the organoazide. Slow expulsion of dinitrogen (N₂) was observed at room temperature to afford a ligand functionalized product via a [3+2] annulation, which can be mediated by a high-valent nitrene intermediate such as a Co^III iminyl (^ArL)CoBr(·N(C₆H₄-p-^tBu)) or Co^IV imido (^ArL)CoBr(N(C₆H₄-p-^tBu)) complex. The presence of the proposed intermediate and its viability as a nitrene group transfer reagent are supported by: (1) exclusive formation of the corresponding aniline-bound complex (^ArL)CoBr(NH₂(C₆H₄-p-^tBu)) when excess 1,4-cyclohexadiene is added; (2) aziridination of styrene; and (3) allylic C–H bond amination of cyclohexene. Unlike (^ArL)CoBr(N₃(C₆H₄-p-^tBu)), a series of alkyl azide-bound Co^II analogues expel N₂ only above 60 °C, affording paramagnetic interme-diates that convert to the corresponding Co-imine complexes via α-H–atom abstraction. The corresponding N₂-released structures were observed via single-crystal-to-crystal transformation, suggesting formation of a Co-nitrenoid intermediate in solid-state. Alternatively, the alkyl azide-bound congeners supported by a more sterically accessible dipyrrinato scaffold ^tBuL (^tBuL = 5-mesityl-(1,9-di-tert-butyl)dipyrrin) facilitate intramolecular 1,3-dipolar cycloaddition as well as C–H amination to furnish 1,2,3-dihydrotriazole and substi-tuted pyrrolidine products, respectively. For the C–H amination, we observe that the temperature required for azide activation varies depending on the presence of weak C–H bonds, suggesting that loss of N₂ is induced by the interaction of the azide moiety with both intra- and intermolecular C–H bonds. These results demonstrate that the alkyl azide-bound cobalt complexes serve as viable species for C–H amination when the C–H bonds are (1) proximal to the azide moiety and (2) sufficiently weak to be activated.

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Research Organization:: Texas A & M Univ., College Station, TX (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES); National Institutes of Health (NIH); Dreyfus Foundation; Harvard University; Welch Foundation; National Science Foundation (NSF)

Grant/Contract Number:: SC0018977; AC02-06CH11357; GM-115815; NSF/CHE-1346572; NSF/DMR-1531283

OSTI ID:: 1780826

Journal Information:: Journal of the American Chemical Society, Vol. 142, Issue 25; ISSN 0002-7863

Publisher:: American Chemical Society (ACS)Copyright Statement

Country of Publication:: United States

Language:: English

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CCDC 2010247: Experimental Crystal Structure Determination Yunjung, Baek,; Anuvab, Das,; Shao-Liang, Zheng, https://doi.org/10.5517/ccdc.csd.cc25gtp5 The current record is supplemented by this dataset	dataset	January 2020
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CCDC 2010249: Experimental Crystal Structure Determination Yunjung, Baek,; Anuvab, Das,; Shao-Liang, Zheng, https://doi.org/10.5517/ccdc.csd.cc25gtr7 The current record is supplemented by this dataset	dataset	January 2020
CCDC 2010250: Experimental Crystal Structure Determination Yunjung, Baek,; Anuvab, Das,; Shao-Liang, Zheng, https://doi.org/10.5517/ccdc.csd.cc25gts8 The current record is supplemented by this dataset	dataset	January 2020
CCDC 2010251: Experimental Crystal Structure Determination Yunjung, Baek,; Anuvab, Das,; Shao-Liang, Zheng, https://doi.org/10.5517/ccdc.csd.cc25gtt9 The current record is supplemented by this dataset	dataset	January 2020
CCDC 2010252: Experimental Crystal Structure Determination Yunjung, Baek,; Anuvab, Das,; Shao-Liang, Zheng, https://doi.org/10.5517/ccdc.csd.cc25gtvb The current record is supplemented by this dataset	dataset	January 2020
CCDC 2010253: Experimental Crystal Structure Determination Yunjung, Baek,; Anuvab, Das,; Shao-Liang, Zheng, https://doi.org/10.5517/ccdc.csd.cc25gtwc The current record is supplemented by this dataset	dataset	January 2020
CCDC 2010254: Experimental Crystal Structure Determination Yunjung, Baek,; Anuvab, Das,; Shao-Liang, Zheng, https://doi.org/10.5517/ccdc.csd.cc25gtxd The current record is supplemented by this dataset	dataset	January 2020
CCDC 2010255: Experimental Crystal Structure Determination Yunjung, Baek,; Anuvab, Das,; Shao-Liang, Zheng, https://doi.org/10.5517/ccdc.csd.cc25gtyf The current record is supplemented by this dataset	dataset	January 2020
CCDC 2010256: Experimental Crystal Structure Determination Yunjung, Baek,; Anuvab, Das,; Shao-Liang, Zheng, https://doi.org/10.5517/ccdc.csd.cc25gtzg The current record is supplemented by this dataset	dataset	January 2020
CCDC 2010257: Experimental Crystal Structure Determination Yunjung, Baek,; Anuvab, Das,; Shao-Liang, Zheng, https://doi.org/10.5517/ccdc.csd.cc25gv0j The current record is supplemented by this dataset	dataset	January 2020
CCDC 2010258: Experimental Crystal Structure Determination Yunjung, Baek,; Anuvab, Das,; Shao-Liang, Zheng, https://doi.org/10.5517/ccdc.csd.cc25gv1k The current record is supplemented by this dataset	dataset	January 2020
CCDC 2010259: Experimental Crystal Structure Determination Yunjung, Baek,; Anuvab, Das,; Shao-Liang, Zheng, https://doi.org/10.5517/ccdc.csd.cc25gv2l The current record is supplemented by this dataset	dataset	January 2020
CCDC 2010260: Experimental Crystal Structure Determination Yunjung, Baek,; Anuvab, Das,; Shao-Liang, Zheng, https://doi.org/10.5517/ccdc.csd.cc25gv3m The current record is supplemented by this dataset	dataset	January 2020

Title: C–H Amination Mediated by Cobalt Organoazide Adducts and the Corresponding Cobalt Nitrenoid Intermediates

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