{"title":"Enantioselective Intermolecular Benzylic C–H Amination under Chiral Paddle-Wheel Diruthenium Catalysis","authors":"Kotoko Makino, Kohei Mori, Shoichi Kiryu, Taku Miyazawa, Yuhei Kumagai, Kosuke Higashida, Masahiro Kojima, Tatsuhiko Yoshino, Shigeki Matsunaga","doi":"10.1021/acscatal.4c06504","DOIUrl":null,"url":null,"abstract":"A catalytic asymmetric intermolecular benzylic C–H amination was achieved under paddle-wheel diruthenium catalysis. A chiral diruthenium catalyst incorporating (<i>S</i>)-TPPTTL (tetraphenylphthaloyl-(<i>S</i>)-<i>tert</i>-leucine) ligand exhibited notable enantioselectivity, and aminated products were obtained with up to 99% ee. Unique chemoselectivity of the chiral diruthenium catalyst was also found for allylbenzene and alkyl-naphthalene substrates, demonstrating the complementary synthetic utility of chiral paddle-wheel Ru(II)–Ru(III) catalysts to Rh(II) counterparts.","PeriodicalId":9,"journal":{"name":"ACS Catalysis ","volume":"41 1","pages":""},"PeriodicalIF":11.3000,"publicationDate":"2024-12-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"ACS Catalysis ","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1021/acscatal.4c06504","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, PHYSICAL","Score":null,"Total":0}
引用次数: 0
Abstract
A catalytic asymmetric intermolecular benzylic C–H amination was achieved under paddle-wheel diruthenium catalysis. A chiral diruthenium catalyst incorporating (S)-TPPTTL (tetraphenylphthaloyl-(S)-tert-leucine) ligand exhibited notable enantioselectivity, and aminated products were obtained with up to 99% ee. Unique chemoselectivity of the chiral diruthenium catalyst was also found for allylbenzene and alkyl-naphthalene substrates, demonstrating the complementary synthetic utility of chiral paddle-wheel Ru(II)–Ru(III) catalysts to Rh(II) counterparts.
期刊介绍：
ACS Catalysis is an esteemed journal that publishes original research in the fields of heterogeneous catalysis, molecular catalysis, and biocatalysis. It offers broad coverage across diverse areas such as life sciences, organometallics and synthesis, photochemistry and electrochemistry, drug discovery and synthesis, materials science, environmental protection, polymer discovery and synthesis, and energy and fuels.
The scope of the journal is to showcase innovative work in various aspects of catalysis. This includes new reactions and novel synthetic approaches utilizing known catalysts, the discovery or modification of new catalysts, elucidation of catalytic mechanisms through cutting-edge investigations, practical enhancements of existing processes, as well as conceptual advances in the field. Contributions to ACS Catalysis can encompass both experimental and theoretical research focused on catalytic molecules, macromolecules, and materials that exhibit catalytic turnover.
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