N-Acylphthalimides: Efficient Acyl Coupling Reagents in Suzuki–Miyaura Cross-Coupling by N–C Cleavage Catalyzed by Pd–PEPPSI Precatalysts

Rahman, Md. Mahbubur; Buchspies, Jonathan; Szostak, Michal

doi:10.3390/catal9020129

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N-Acylphthalimides: Efficient Acyl Coupling Reagents in Suzuki–Miyaura Cross-Coupling by N–C Cleavage Catalyzed by Pd–PEPPSI Precatalysts

Md. Mahbubur Rahman

^†,

Jonathan Buchspies

^† and

Michal Szostak

Department of Chemistry, Rutgers University, 73 Warren Street, Newark, NJ 07102, USA

Author to whom correspondence should be addressed.

^†

These authors contributed equally to this work.

Catalysts 2019, 9(2), 129; https://doi.org/10.3390/catal9020129

Received: 21 December 2018 / Revised: 8 January 2019 / Accepted: 16 January 2019 / Published: 1 February 2019

(This article belongs to the Special Issue Catalysts for Suzuki–Miyaura Coupling Reaction)

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Abstract

We report a general, highly selective method for Suzuki–Miyaura cross-coupling of N-acylphthalimides via N–C(O) acyl cleavage catalyzed by Pd–PEPPSI-type precatalysts. Of broad synthetic interest, the method introduces N-acylphthalimides as new, bench-stable, highly reactive, twist-controlled, amide-based precursors to acyl-metal intermediates. The reaction delivers functionalized biaryl ketones by acylative Suzuki–Miyaura cross-coupling with readily available boronic acids. Studies demonstrate that cheap, easily prepared, and broadly applicable Pd–PEPPSI-type precatalysts supported by a sterically demanding IPr (1,3-Bis-(2,6-diisopropylphenyl)imidazol-2-ylidene) ancillary ligand provide high yields in this reaction. Preliminary selectivity studies and the effect of Pd–N-heterocyclic carbenes (NHC) complexes with allyl-type throw-away ligands are described. We expect that N-acylphthalimides will find significant use as amide-based acyl coupling reagents and cross-coupling precursors to acyl-metal intermediates. View Full-Text

Keywords: Suzuki cross-coupling; amide bond N–C cleavage; N–C activation; amide bond twist; acylation; ketones; acylative cross-coupling; palladium; N-heterocyclic carbene; Pd–PEPPSI

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MDPI and ACS Style

Rahman, M.M.; Buchspies, J.; Szostak, M. N-Acylphthalimides: Efficient Acyl Coupling Reagents in Suzuki–Miyaura Cross-Coupling by N–C Cleavage Catalyzed by Pd–PEPPSI Precatalysts. Catalysts 2019, 9, 129. https://doi.org/10.3390/catal9020129

AMA Style

Rahman MM, Buchspies J, Szostak M. N-Acylphthalimides: Efficient Acyl Coupling Reagents in Suzuki–Miyaura Cross-Coupling by N–C Cleavage Catalyzed by Pd–PEPPSI Precatalysts. Catalysts. 2019; 9(2):129. https://doi.org/10.3390/catal9020129

Chicago/Turabian Style

Rahman, Md. M., Jonathan Buchspies, and Michal Szostak. 2019. "N-Acylphthalimides: Efficient Acyl Coupling Reagents in Suzuki–Miyaura Cross-Coupling by N–C Cleavage Catalyzed by Pd–PEPPSI Precatalysts" Catalysts 9, no. 2: 129. https://doi.org/10.3390/catal9020129

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N-Acylphthalimides: Efficient Acyl Coupling Reagents in Suzuki–Miyaura Cross-Coupling by N–C Cleavage Catalyzed by Pd–PEPPSI Precatalysts

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