ORGANIC CHEMISTRY FRONTIERS REVIEW Cite this: Org. Chem. Front., 2020, 7, 1022 Received 19th December 2019, Accepted 10th March 2020 DOI: 10.1039/c9qo01497g rsc.li/frontiers-organic Chelation-assisted transition metal-catalysed C–H chalcogenylations Wenbo Ma, * a Nikolaos Kaplaneris, b Xinyue Fang, a Linghui Gu, a Ruhuai Mei c and Lutz Ackermann * b The development of convenient and mild chalcogenylation reactions for the preparation of unsymmetri- cal diaryl sulfides and diaryl selenides has received significant attention in recent years due to their preva- lence in natural products, organic molecular syntheses, catalysis, drug candidates and functional materials. In contrast with conventional organic transformations which largely relyon the inherent reactiv- ity of functional groups, transition metal-catalysed direct C–H functionalizations have emerged as a powerful strategy that eliminates prefunctionalised starting materials and thus leads to more atom- and step-economical processes. This review summarizes the recent advances in C–S and C–Se formations via transition metal-catalyzed C–H functionalization utilizing directing groups to control the site-selecti- vity until autumn 2019. Typical examples are listed and mechanistic aspects are discussed in detail. 1. Introduction Aryl sulfides and aryl selenides are ubiquitous structural motifs that have been identified as potent drug candidates, bioactive molecules, 1–5 and fluorescent probes. 6,7 They also play an indispensable role in molecular syntheses 8–10 and organocatalysis. 11–16 For instance, various sulfur- and sel- enium-containing molecules have been identified as impor- tant therapeutic compounds with bioactivities ranging from antiviral, anti-inflammatory, antibacterial, anticonvulsant, Wenbo Ma Wenbo Ma was born in Hebei province, P. R. China. After he obtained his B.Sc. degree in pharmacy sciences from the North China University of Science and Technology and M. Sc. in medicinal chemistry from the West China School of Pharmacy, Sichuan University, he joined Prof. Dr Lutz Ackermann’s research group at the Georg-August University of Göttingen where he obtained his Ph.D. degree in 2015. Afterwards he was appointed as a professor at the Sichuan Industrial Institute of Antibiotics, Chengdu University. His current research interests are focused on medicinal chemistry and methodology study on transition-metal catalyzed C–H functionalization. Nikolaos Kaplaneris Nikolaos Kaplaneris was born in 1992 in Athens, Greece. He received his bachelor’s degree in chemistry from the National and Kapodistrian University of Athens in 2014. He obtained his master’s degree in organic chem- istry from the same university in 2016 following studies in the area of organocatalysis and photochemistry under the super- vision of Prof. Christoforos G. Kokotos. In the same year, he joined the group of Prof. Lutz Ackermann at the Georg-August-Universita ¨t Göttingen as a PhD student, working on late-stage peptide diversification and remote functionalization. a Antibiotics Research and Re-evaluation Key Laboratory of Sichuan Province, Sichuan Industrial Institute of Antibiotics, Chengdu University, Chengdu, 610052, P. R. China. E-mail: wenboma@hotmail.com b Institute fuer Organische und Biomolekular Chemie, Georg-August-Universitaet Goettingen, Tammannstrasse 2, 37077 Goettingen, Germany. E-mail: Lutz.Ackermann@chemie.uni-goettingen.de c College of Pharmacy and Biological Engineering Chengdu University, Chengdu, 610106, P. R. China 1022 | Org. Chem. Front. , 2020, 7, 1022–1060 This journal is © the Partner Organisations 2020 Published on 11 March 2020. Downloaded on 9/24/2021 1:50:37 PM. View Article Online View Journal | View Issue