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Organische Chemie

Wellcome to Nachtsheims Group


The inside cover picture, provided by Pericàs and Nachtsheim, illustrates the development of novel C1-symmetric iodoarenes as precursors for chiral aryl-λ3-iodanes. The synthesis of these structures is highly modular and allows easy modification on all major substituents, namely the arene, the alkyl ether and the terminal triazole. This is not only the first example for a triazole-based chiral iodoarene but also the so far most efficient C1-symmetric catalyst for the oxidative enantioselective spirocyclization of 1-naphtholcarboxylic acids to spirolactones. C. Hempel, C. Maichle-Moessmer, M. A. Pericàs, B. J. Nachtsheim, Adv. Synth. Catal2017359, 2931-2941; DOI: 10.1002/adsc.201700246.

C−H Activation Directing groups are crucial in transition metal-catalyzed C−H activations to control regio-and stereoselectivity. So far, free amines have rarely been used as directing groups since they tend to deactivate the transition metal or undergo undesired side reactions. We demonstrate that free amines in anilines can be used as directing groups in delicate C−H activating alkynylations to give versatile 1,3-enynes in excellent yields and stereoselectivities using highly reactive hypervalent iodine-based alkynylation reagents . L. D. Caspers, P. Finkbeiner, B. J. Nachtsheim, Chem. Eur.J.2017, 23, 2748 –2752; DOI:  10.1002/chem.201781262