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Electrocatalytic Transfer Hydrogenation of 1-Octene with [( tBu PCP)Ir(H)(Cl)] and Water.

التفاصيل البيبلوغرافية
العنوان: Electrocatalytic Transfer Hydrogenation of 1-Octene with [( tBu PCP)Ir(H)(Cl)] and Water.
المؤلفون: Mollik P; Technical University of Munich, TUM School of Natural Sciences, Department of Chemistry, Chair of Inorganic and Metal-Organic Chemistry, Lichtenbergstr. 4, 85748, Garching, Germany., Drees M; Technical University of Munich, TUM School of Natural Sciences, Department of Chemistry, Chair of Inorganic and Metal-Organic Chemistry, Lichtenbergstr. 4, 85748, Garching, Germany., Frantz AM; Technical University of Munich, TUM School of Natural Sciences, Department of Chemistry, Chair of Inorganic and Metal-Organic Chemistry, Lichtenbergstr. 4, 85748, Garching, Germany., Halter DP; Technical University of Munich, TUM School of Natural Sciences, Department of Chemistry, Chair of Inorganic and Metal-Organic Chemistry, Lichtenbergstr. 4, 85748, Garching, Germany.
المصدر: Angewandte Chemie (International ed. in English) [Angew Chem Int Ed Engl] 2024 Jul 29; Vol. 63 (31), pp. e202317844. Date of Electronic Publication: 2024 Jul 01.
نوع المنشور: Journal Article
اللغة: English
بيانات الدورية: Publisher: Wiley-VCH Country of Publication: Germany NLM ID: 0370543 Publication Model: Print-Electronic Cited Medium: Internet ISSN: 1521-3773 (Electronic) Linking ISSN: 14337851 NLM ISO Abbreviation: Angew Chem Int Ed Engl Subsets: PubMed not MEDLINE; MEDLINE
أسماء مطبوعة: Publication: <2004-> : Weinheim : Wiley-VCH
Original Publication: Weinheim/Bergstr. : New York, : Verlag Chemie ; Academic Press, c1962-
مستخلص: Electrocatalytic hydrogenation of 1-octene as non-activated model substrate with neutral water as H-donor is reported, using [( tBu PCP)Ir(H)(Cl)] (1) as the catalyst, to form octane with high faradaic efficiency (FE) of 96 % and a k obs of 87 s -1 . Cyclic voltammetry with 1 revealed that two subsequent reductions trigger the elimination of Cl - and afford the highly reactive anionic Ir(I) hydride complex [( tBu PCP)Ir(H)] - (2), a previously merely proposed intermediate for which we now report first experimental data by mass spectrometry. In absence of alkene, the stoichiometric electrolysis of 1 in THF with water selectively affords the Ir(III) dihydride complex [( tBu PCP)Ir(H) 2 ] (3) in 88 % FE from the reaction of 2 with H 2 O. Complex 3 then hydrogenates the alkene in classical fashion. The presented electro-hydrogenation works with extremely high FE, because the iridium hydrides are water stable, which prevents H 2 formation. Even in strongly alkaline conditions (Bu 4 NOH added), the electro-hydrogenation of 1-octene with 1 also proceeds cleanly (89 % FE), suggesting a highly robust process that may rely on H 2 O activation, reminiscent to transfer hydrogenation pathways, instead of classical H + reduction. DFT calculations confirmed oxidative addition of H 2 O as a key step in this context.
(© 2024 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH.)
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معلومات مُعتمدة: Feodor Lynen Return Fellowship Alexander von Humboldt-Stiftung; Liebig Fellowship Fonds der Chemischen Industrie; TUM Junior Fellow Funds Technische Universität München
فهرسة مساهمة: Keywords: Ir(III)-pincer; anionic Ir(I) hydride; cyclic voltammetry; electro-synthesis; electrochemical hydrogenation
تواريخ الأحداث: Date Created: 20240517 Latest Revision: 20240722
رمز التحديث: 20240723
DOI: 10.1002/anie.202317844
PMID: 38757787
قاعدة البيانات: MEDLINE
الوصف
تدمد:1521-3773
DOI:10.1002/anie.202317844