title: Taming hypervalent bonds and strained rings for catalysis and synthesis.
abstract: 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.
authors.affiliation: Ecole Polytechnique Fédérale de Lausanne Laboratory of Catalysis and Organic Synthesis EPFL SB ISIC LCSO BCH 4306 CH-1015 Lausanne, Switzerland.
authors.forename: Florian
authors.initials: F
authors.lastname: de Nanteuil
authors.affiliation: Ecole Polytechnique Fédérale de Lausanne Laboratory of Catalysis and Organic Synthesis EPFL SB ISIC LCSO BCH 4306 CH-1015 Lausanne, Switzerland.
authors.forename: Yifan
authors.initials: Y
authors.lastname: Li
authors.affiliation: Ecole Polytechnique Fédérale de Lausanne Laboratory of Catalysis and Organic Synthesis EPFL SB ISIC LCSO BCH 4306 CH-1015 Lausanne, Switzerland.
authors.forename: Maria Victoria
authors.initials: MV
authors.lastname: Vita
authors.affiliation: Ecole Polytechnique Fédérale de Lausanne Laboratory of Catalysis and Organic Synthesis EPFL SB ISIC LCSO BCH 4306 CH-1015 Lausanne, Switzerland.
authors.forename: Reto
authors.initials: R
authors.lastname: Frei
authors.affiliation: Ecole Polytechnique Fédérale de Lausanne Laboratory of Catalysis and Organic Synthesis EPFL SB ISIC LCSO BCH 4306 CH-1015 Lausanne, Switzerland.
authors.forename: Eloisa
authors.initials: E
authors.lastname: Serrano
authors.affiliation: Ecole Polytechnique Fédérale de Lausanne Laboratory of Catalysis and Organic Synthesis EPFL SB ISIC LCSO BCH 4306 CH-1015 Lausanne, Switzerland.
authors.forename: Sophie
authors.initials: S
authors.lastname: Racine
authors.affiliation: Ecole Polytechnique Fédérale de Lausanne Laboratory of Catalysis and Organic Synthesis EPFL SB ISIC LCSO BCH 4306 CH-1015 Lausanne, Switzerland. jerome.waser@epfl.ch.
authors.forename: Jérôme
authors.initials: J
authors.lastname: Waser