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Palladium-Catalyzed Selective Five-Fold Cascade Arylation of the 12-Vertex Monocarborane Anion by B–H Activation

  • Furong Lin
    Furong Lin
    Department of Chemistry, Zhejiang University, 38 Zheda Road, 310027 Hangzhou, People’s Republic of China
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  • , 
  • Jing-Lu Yu
    Jing-Lu Yu
    Department of Chemistry, Zhejiang University, 38 Zheda Road, 310027 Hangzhou, People’s Republic of China
    More by Jing-Lu Yu
  • , 
  • Yunjun Shen
    Yunjun Shen
    Department of Chemistry, Zhejiang University, 38 Zheda Road, 310027 Hangzhou, People’s Republic of China
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  • , 
  • Shuo-Qing Zhang
    Shuo-Qing Zhang
    Department of Chemistry, Zhejiang University, 38 Zheda Road, 310027 Hangzhou, People’s Republic of China
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    Orcidhttp://orcid.org/0000-0002-7617-3042
  • , 
  • Bernhard Spingler
    Bernhard Spingler
    Department of Chemistry, University of Zurich, Winterthurerstrasse 190, 8057 Zurich, Switzerland
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    Orcidhttp://orcid.org/0000-0003-3402-2016
  • , 
  • Jiyong Liu
    Jiyong Liu
    Department of Chemistry, Zhejiang University, 38 Zheda Road, 310027 Hangzhou, People’s Republic of China
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  • , 
  • Xin Hong*
    Xin Hong
    Department of Chemistry, Zhejiang University, 38 Zheda Road, 310027 Hangzhou, People’s Republic of China
    *[email protected]
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    Orcidhttp://orcid.org/0000-0003-4717-2814
  • , and 
  • Simon Duttwyler*
    Simon Duttwyler
    Department of Chemistry, Zhejiang University, 38 Zheda Road, 310027 Hangzhou, People’s Republic of China
    *[email protected]
    More by Simon Duttwyler
    Orcidhttp://orcid.org/0000-0001-9851-4920
Cite this: J. Am. Chem. Soc. 2018, 140, 42, 13798–13807
Publication Date (Web):September 19, 2018
https://doi.org/10.1021/jacs.8b07872
Copyright © 2018 American Chemical Society
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    Abstract

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    A series of cage penta-arylated carboranes have been synthesized by palladium-catalyzed intermolecular coupling of the C-carboxylic acid of the monocarba-closo-dodecaborate anion [CB11H12]− with iodoarenes by direct cage B–H bond functionalization. These transformations set a record in terms of one-pot directing group-mediated activation of inert bonds in a single molecule. The methodology is characterized by high yields, good functional group tolerance, and complete cage regioselectivity. The directing group COOH can be easily removed during or after the intermolecular coupling reaction. The mechanistic pathways were probed using density functional theory calculations. A Pd(II)–Pd(IV)–Pd(II) catalytic cycle is proposed, in which initial coupling is followed by preferred B–H activation of the adjacent boron vertex, and continuation of this selectivity results in a continuous walking process of the palladium center. The methodology opens a new avenue toward building blocks with 5-fold symmetry.

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    The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/jacs.8b07872.

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