Nitrogen Atom Transfer Catalysis by Metallonitrene C−H Insertion: Photocatalytic Amidation of Aldehydes

Schmidt‐Räntsch, Till; Verplancke, Hendrik; Lienert, Jonas N.; Demeshko, Serhiy; Otte, Matthias; Van Trieste, III, Gerard P.; Reid, Kaleb A.; Reibenspies, Joseph H.; Powers, David C.; Holthausen, Max C.; Schneider, Sven

doi:10.1002/ange.202115626

Title: Nitrogen Atom Transfer Catalysis by Metallonitrene C−H Insertion: Photocatalytic Amidation of Aldehydes

Journal Article · 14 January 2022 · Angewandte Chemie

DOI: https://doi.org/10.1002/ange.202115626 · OSTI ID:1840633

Schmidt‐Räntsch, Till ^[1]; Verplancke, Hendrik ^[2]; Lienert, Jonas N. ^[2]; Demeshko, Serhiy ^[1]; Otte, Matthias ^[1]; Van Trieste, III, Gerard P. ^[3]; Reid, Kaleb A. ^[3]; Reibenspies, Joseph H. ^[3]; Powers, David C. ^[3]; Holthausen, Max C. ^[2];

^[1]

Institut für Anorganische Chemie Universität Göttingen Tammannstraße 4 37077 Göttingen Germany
Institut für Anorganische und Analytische Chemie Goethe-Universität Max-von-Laue-Straße 7 60438 Frankfurt am Main Germany
Department of Chemistry Texas A&,M University 3255 TAMU College Station TX 77843 USA

Abstract C−H amination and amidation by catalytic nitrene transfer are well‐established and typically proceed via electrophilic attack of nitrenoid intermediates. In contrast, the insertion of (formal) terminal nitride ligands into C−H bonds is much less developed and catalytic nitrogen atom transfer remains unknown. We here report the synthesis of a formal terminal nitride complex of palladium. Photocrystallographic, magnetic, and computational characterization support the assignment as an authentic metallonitrene (Pd−N) with a diradical nitrogen ligand that is singly bonded to Pd ^II . Despite the subvalent nitrene character, selective C−H insertion with aldehydes follows nucleophilic selectivity. Transamidation of the benzamide product is enabled by reaction with N ₃ SiMe ₃ . Based on these results, a photocatalytic protocol for aldehyde C−H trimethylsilylamidation was developed that exhibits inverted, nucleophilic selectivity as compared to typical nitrene transfer catalysis. This first example of catalytic C−H nitrogen atom transfer offers facile access to primary amides after deprotection.

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Sponsoring Organization:: USDOE

Grant/Contract Number:: SC0018977; AC02-06CH11357

OSTI ID:: 1840633

Journal Information:: Angewandte Chemie, Journal Name: Angewandte Chemie Journal Issue: 9 Vol. 134; ISSN 0044-8249

Publisher:: Wiley Blackwell (John Wiley & Sons)Copyright Statement

Country of Publication:: Germany

Language:: English

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