Preparation of chiral-at-metal catalysts and their use in asymmetric photoredox chemistry

Nature Protocols
Jiajia MaEric Meggers

Abstract

Asymmetric catalysis is a powerful approach for the synthesis of optically active compounds, and visible light constitutes an abundant source of energy to enable chemical transformations, which are often triggered by photoinduced electron transfer (photoredox chemistry). Recently, bis-cyclometalated iridium(III) and rhodium(III) complexes were introduced as a novel class of catalysts for combining asymmetric catalysis with visible-light-induced photoredox chemistry. These catalysts are attractive because of their unusual feature of chirality originating exclusively from a stereogenic metal center, which offers the prospect of an especially effective asymmetric induction upon direct coordination of the substrate to the metal center. As these chiral catalysts contain only achiral ligands, special strategies are required for their synthesis. In this protocol, we describe strategies for preparing two types of chiral-at-metal catalysts, namely the Λ- and Δ-enantiomers (left- and right-handed propellers, respectively) of the iridium complex IrS and the rhodium complex RhS. Both contain two cyclometalating 5-tert-butyl-2-phenylbenzothiazoles in addition to two acetonitrile ligands and a hexafluorophosphate counterion. The two cyclomet...Continue Reading

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Citations

May 9, 2019·Chemical Communications : Chem Comm·Romane ManguinOlivier Baslé
Oct 2, 2019·Dalton Transactions : an International Journal of Inorganic Chemistry·Jasmin BuschClaudia Bizzarri
Sep 22, 2019·Chemistry : a European Journal·Philipp S SteinlandtEric Meggers
May 28, 2020·Organic & Biomolecular Chemistry·Bor-Cherng Hong
May 28, 2020·Dalton Transactions : an International Journal of Inorganic Chemistry·Tatyana E KokinaMark B Bushuev
Sep 25, 2019·Nature Chemistry·Huaiyi HuangPeter J Sadler
Jul 3, 2020·The Journal of Chemical Physics·Jason J SorensenMichael D Morse
Apr 4, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Sebastian BrunenEric Meggers
May 31, 2021·Dalton Transactions : an International Journal of Inorganic Chemistry·Yoshiki JinsenjiHisako Sato
Aug 12, 2021·Journal of the American Chemical Society·Hannah SayreRobert R Knowles
Mar 7, 2019·Accounts of Chemical Research·Xiaoqiang Huang, Eric Meggers
Oct 5, 2021·Chemical Reviews·Matthew J GenzinkTehshik P Yoon
Oct 9, 2021·Chemical Reviews·Kelvin Pak Shing CheungVladimir Gevorgyan
Nov 5, 2021·Chemical Communications : Chem Comm·Janis Mikelis ZakisJoanna Wencel-Delord

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