Scalable and safe synthetic organic electroreduction inspired by Li-ion battery chemistry.

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    • Abstract:
      Reductive electrosynthesis has faced long-standing challenges in applications to complex organic substrates at scale. Here, we show how decades of research in lithium-ion battery materials, electrolytes, and additives can serve as an inspiration for achieving practically scalable reductive electrosynthetic conditions for the Birch reduction. Specifically, we demonstrate that using a sacrificial anode material (magnesium or aluminum), combined with a cheap, nontoxic, and water-soluble proton source (dimethylurea), and an overcharge protectant inspired by battery technology [tris(pyrrolidino)phosphoramide] can allow for multigram-scale synthesis of pharmaceutically relevant building blocks. We show how these conditions have a very high level of functional-group tolerance relative to classical electrochemical and chemical dissolving-metal reductions. Finally, we demonstrate that the same electrochemical conditions can be applied to other dissolving metal–type reductive transformations, including McMurry couplings, reductive ketone deoxygenations, and epoxide openings. [ABSTRACT FROM AUTHOR]
    • Abstract:
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    • Full Text Word Count:
      5512
    • ISSN:
      0036-8075
    • Accession Number:
      10.1126/science.aav5606
    • Accession Number:
      134902599
  • Citations
    • ABNT:
      PETERS, B. K. et al. Scalable and safe synthetic organic electroreduction inspired by Li-ion battery chemistry. Science, [s. l.], v. 363, n. 6429, p. 838–845, 2019. DOI 10.1126/science.aav5606. Disponível em: http://search.ebscohost.com/login.aspx?direct=true&site=eds-live&db=asn&AN=134902599&custid=s8280428. Acesso em: 7 dez. 2019.
    • AMA:
      Peters BK, Rodriguez KX, Reisberg SH, et al. Scalable and safe synthetic organic electroreduction inspired by Li-ion battery chemistry. Science. 2019;363(6429):838-845. doi:10.1126/science.aav5606.
    • APA:
      Peters, B. K., Rodriguez, K. X., Reisberg, S. H., Beil, S. B., Hickey, D. P., Kawamata, Y., … Baran, P. S. (2019). Scalable and safe synthetic organic electroreduction inspired by Li-ion battery chemistry. Science, 363(6429), 838–845. https://doi.org/10.1126/science.aav5606
    • Chicago/Turabian: Author-Date:
      Peters, Byron K., Kevin X. Rodriguez, Solomon H. Reisberg, Sebastian B. Beil, David P. Hickey, Yu Kawamata, Michael Collins, et al. 2019. “Scalable and Safe Synthetic Organic Electroreduction Inspired by Li-Ion Battery Chemistry.” Science 363 (6429): 838–45. doi:10.1126/science.aav5606.
    • Harvard:
      Peters, B. K. et al. (2019) ‘Scalable and safe synthetic organic electroreduction inspired by Li-ion battery chemistry’, Science, 363(6429), pp. 838–845. doi: 10.1126/science.aav5606.
    • Harvard: Australian:
      Peters, BK, Rodriguez, KX, Reisberg, SH, Beil, SB, Hickey, DP, Kawamata, Y, Collins, M, Starr, J, Chen, L, Udyavara, S, Klunder, K, Gorey, TJ, Anderson, SL, Neurock, M, Minteer, SD & Baran, PS 2019, ‘Scalable and safe synthetic organic electroreduction inspired by Li-ion battery chemistry’, Science, vol. 363, no. 6429, pp. 838–845, viewed 7 December 2019, .
    • MLA:
      Peters, Byron K., et al. “Scalable and Safe Synthetic Organic Electroreduction Inspired by Li-Ion Battery Chemistry.” Science, vol. 363, no. 6429, Feb. 2019, pp. 838–845. EBSCOhost, doi:10.1126/science.aav5606.
    • Chicago/Turabian: Humanities:
      Peters, Byron K., Kevin X. Rodriguez, Solomon H. Reisberg, Sebastian B. Beil, David P. Hickey, Yu Kawamata, Michael Collins, et al. “Scalable and Safe Synthetic Organic Electroreduction Inspired by Li-Ion Battery Chemistry.” Science 363, no. 6429 (February 22, 2019): 838–45. doi:10.1126/science.aav5606.
    • Vancouver/ICMJE:
      Peters BK, Rodriguez KX, Reisberg SH, Beil SB, Hickey DP, Kawamata Y, et al. Scalable and safe synthetic organic electroreduction inspired by Li-ion battery chemistry. Science [Internet]. 2019 Feb 22 [cited 2019 Dec 7];363(6429):838–45. Available from: http://search.ebscohost.com/login.aspx?direct=true&site=eds-live&db=asn&AN=134902599&custid=s8280428