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A Metallaphotoredox Method for the Expansion of Benzyl SAR on Electron-Deficient Amines

  • Meghan D. Shea
    Meghan D. Shea
    Discovery Chemistry, Merck & Co., Inc., 33 Avenue Louis Pasteur, Boston, Massachusetts 02115, United States
  • Umar Faruk Mansoor
    Umar Faruk Mansoor
    Discovery Chemistry, Merck & Co., Inc., 33 Avenue Louis Pasteur, Boston, Massachusetts 02115, United States
  • Brett A. Hopkins*
    Brett A. Hopkins
    Discovery Chemistry, Merck & Co., Inc., 33 Avenue Louis Pasteur, Boston, Massachusetts 02115, United States
    *Email: [email protected].
Cite this: Org. Lett. 2020, XXXX, XXX, XXX-XXX
Publication Date (Web):January 28, 2020
https://doi.org/10.1021/acs.orglett.9b04587
Copyright © 2020 American Chemical Society
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Abstract

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A metallaphotoredox reaction is described that allows for the efficient exploration of benzyl structure-activity relationships on electron-deficient amines. Typically, accessing a variety of benzyl groups on these substrates can be difficult due to the limited availability of the prerequisite building blocks, namely benzyl halides. However, the use of aryl bromides in this metallaphotoredox reaction allows for greater diversity in the benzyl piece. The reaction scope is discussed herein, including conditions for product scaleup using flow.

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  • Experimental procedures, characterization data for all new compounds (starting material and final products), and 1H and 13C NMR spectra for all compounds (PDF)

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