Decarboxylative Alkynylation and Cyanation of Carboxylic Acids using Photoredox Catalysis and Hypervalent Iodine Reagents

Authors

  • Franck Le Vaillant Laboratory of Catalysis and Organic Synthesis Ecole Polytechnique Fédérale de Lausanne EPFL SB ISIC LCSO, BCH 4306 CH-1015 Lausanne, Switzerland
  • Jérôme Waser Laboratory of Catalysis and Organic Synthesis Ecole Polytechnique Fédérale de Lausanne EPFL SB ISIC LCSO, BCH 4306 CH-1015 Lausanne, Switzerland. jerome.waser@epfl.ch

DOI:

https://doi.org/10.2533/chimia.2017.226

Keywords:

Decarboxylative alkynylation, Decarboxylative cyanation, Mechanistic studies, Hypervalent iodine reagent, Photoredox catalysis

Abstract

Alkynes and nitriles are important functional groups that serve as versatile building blocks in organic synthesis and find applications in material and medicinal sciences. A convenient and straightforward access to both classes of compounds under mild conditions is, therefore, highly desirable. Herein, we disclose the decarboxylative alkynylation and cyanation of broadly available carboxylic acids using photoredox catalysis and hypervalent iodine reagents. Choices of both catalysts and reagents were crucial. Computational and experimental studies revealed two different possible mechanisms that are dictated by the oxidation potential of the reagents: radical for alkynylation, ionic for cyanation.

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Published

2017-04-26

How to Cite

[1]
F. L. Vaillant, J. Waser, Chimia 2017, 71, 226, DOI: 10.2533/chimia.2017.226.