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Open Access Taming Hypervalent Bonds and Strained Rings for Catalysis and Synthesis

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Improving the synthesis of complex organic molecules is essential for progress in many fields such as medicine, agrochemicals or materials. Since 2007, our laboratory has been focusing on the development of non-classical bond disconnections based on the use of small, energy-loaded organic molecules: hypervalent iodine reagents and strained rings. In this overview article, we report our progress since 2011 in these areas. The use of cyclic hypervalent iodine reagents has been extended to the C2-selective alkynylation of indoles, the domino cyclization alkynylation of allenes, the alkynylation of thiols and the azidation of carbonyl compounds. Amino-substituted aminocyclopropanes and aminocyclobutanes were used in [3+2] and [4+2] annulations to access nitrogen-rich building blocks, including nucleoside analogues. The first example of dynamic kinetic [3+2] annulation of aminocyclopropanes with both enol ethers and aldehydes was also reported.

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Keywords: ACETYLENES; ACTIVATED CYCLOPROPANES; CATALYSIS; HYPERVALENT IODINE; SYNTHESIS

Document Type: Research Article

Affiliations: 1: Ecole Polytechnique Fédérale de Lausanne Laboratory of Catalysis and Organic Synthesis EPFL SB ISIC LCSO BCH 4306 CH-1015 Lausanne, Switzerland 2: Ecole Polytechnique Fédérale de Lausanne Laboratory of Catalysis and Organic Synthesis EPFL SB ISIC LCSO BCH 4306 CH-1015 Lausanne, Switzerland. [email protected]

Publication date: 01 August 2014

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  • International Journal for Chemistry and Official Membership Journal of the Swiss Chemical Society (SCS) and its Divisions

    CHIMIA, a scientific journal for chemistry in the broadest sense, is published 10 times a year and covers the interests of a wide and diverse readership. Contributions from all fields of chemistry and related areas are considered for publication in the form of Review Articles and Notes. A characteristic feature of CHIMIA are the thematic issues, each devoted to an area of great current significance.

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