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Devaraj K, Ingner FJL, Sollert C, et al. Arynes and Their Precursors from Arylboronic Acids via Catalytic C-H Silylation. J Org Chem. 2019;84(9):5863-5871doi: 10.1021/acs.joc.9b00221.
Devaraj, K., Ingner, F. J. L., Sollert, C., Gates, P. J., Orthaber, A., & Pilarski, L. T. (2019). Arynes and Their Precursors from Arylboronic Acids via Catalytic C-H Silylation. The Journal of organic chemistry, 84(9), 5863-5871. https://doi.org/10.1021/acs.joc.9b00221
Devaraj, Karthik, et al. "Arynes and Their Precursors from Arylboronic Acids via Catalytic C-H Silylation." The Journal of organic chemistry vol. 84,9 (2019): 5863-5871. doi: https://doi.org/10.1021/acs.joc.9b00221
Devaraj K, Ingner FJL, Sollert C, Gates PJ, Orthaber A, Pilarski LT. Arynes and Their Precursors from Arylboronic Acids via Catalytic C-H Silylation. J Org Chem. 2019 May 03;84(9):5863-5871. doi: 10.1021/acs.joc.9b00221. Epub 2019 Mar 29. PMID: 30835118.
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J Org Chem. 2019 May 03;84(9):5863-5871. doi: 10.1021/acs.joc.9b00221. Epub 2019 Mar 29.

Arynes and Their Precursors from Arylboronic Acids via Catalytic C-H Silylation.

The Journal of organic chemistry

Karthik Devaraj, Fredric J L Ingner, Carina Sollert, Paul J Gates, Andreas Orthaber, Lukasz T Pilarski

Affiliations

  1. Department of Chemistry - BMC , Uppsala University , Box 576, Uppsala 75-123 , Sweden.
  2. School of Chemistry , University of Bristol , Cantock's Close, Clifton, Bristol BS8 1TS , United Kingdom.
  3. Department of Chemistry, Ångström Laboratories , Uppsala University , Box 523, Uppsala 75-120 , Sweden.

PMID: 30835118 DOI: 10.1021/acs.joc.9b00221

Abstract

A new, operationally simple approach is presented to access arynes and their fluoride-activated precursors based on Ru-catalyzed C-H silylation of arylboronates. Chromatographic purification may be deferred until after aryne capture, rendering the arylboronates de facto precursors. Access to various new arynes and their derivatives is demonstrated, including, for the first time, those based on a 2,3-carbazolyne and 2,3-fluorenyne core, which pave the way for novel derivatizations of motifs relevant to materials chemistry.

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