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Aryl Halide Radical Clocks as Probes of Stannylene/Aryl Halide C–H Activation Rates

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Abstract

Using the radical cyclization induced by the reaction of (1) with 1-(but-3-en-1-yloxy)-2-iodobenzene, we have determined the rate of allylic and propargylic C–H activation to be 1.1 ± 0.2 × 108 M−1 s−1. The rate of oxidative addition of aryl halide with 1 was estimated to be 107–108 M−1 s−1. The radical cyclization involving 1 and 1-(allyloxy)-2-iodobenzene proceeds quantitatively, indicating that the rate of cyclization (9.6 × 109 s−1) is faster than the rate of hydrocarbon/alkene/alkyne C–H abstraction.

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Acknowledgments

This work was supported by National Science Foundation Grant CHE-0453849.

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Authors and Affiliations

  1. Chemistry Department, University of Michigan, 930 N University, Ann Arbor, MI, 48109-1055, USA

    Ajdin Kavara, Michael M. Kheir, Jeff W. Kampf & Mark M. Banaszak Holl

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  1. Ajdin Kavara
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  2. Michael M. Kheir
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  3. Jeff W. Kampf
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  4. Mark M. Banaszak Holl
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Correspondence to Mark M. Banaszak Holl.

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The authors dedicate this paper to the memory of Prof. Dwight A. Sweigart.

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Kavara, A., Kheir, M.M., Kampf, J.W. et al. Aryl Halide Radical Clocks as Probes of Stannylene/Aryl Halide C–H Activation Rates. J Inorg Organomet Polym 24, 250–257 (2014). https://doi.org/10.1007/s10904-013-9990-y

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