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Amide Activation in Ground and Excited States

Pd-Catalyzed Suzuki-Miyaura Cross-Coupling of Pentafluorophenyl Esters

Department of Chemistry, Rutgers University, 73 Warren Street, Newark, NJ 07102, USA
Authors to whom correspondence should be addressed.
Molecules 2018, 23(12), 3134;
Received: 12 October 2018 / Revised: 15 November 2018 / Accepted: 23 November 2018 / Published: 29 November 2018
(This article belongs to the Special Issue Amide Bond Activation)
Although the palladium-catalyzed Suzuki-Miyaura cross-coupling of aryl esters has received significant attention, there is a lack of methods that utilize cheap and readily accessible Pd-phosphane catalysts, and can be routinely carried out with high cross-coupling selectivity. Herein, we report the first general method for the cross-coupling of pentafluorophenyl esters (pentafluorophenyl = pfp) by selective C–O acyl cleavage. The reaction proceeds efficiently using Pd(0)/phosphane catalyst systems. The unique characteristics of pentafluorophenyl esters are reflected in the fully selective cross-coupling vs. phenolic esters. Of broad synthetic interest, this report establishes pentafluorophenyl esters as new, highly reactive, bench-stable, economical, ester-based, electrophilic acylative reagents via acyl-metal intermediates. Mechanistic studies strongly support a unified reactivity scale of acyl electrophiles by C(O)–X (X = N, O) activation. The reactivity of pfp esters can be correlated with barriers to isomerization around the C(acyl)–O bond. View Full-Text
Keywords: Suzuki-Miyaura; cross-coupling; aryl esters; C–O activation; Pd-catalysis Suzuki-Miyaura; cross-coupling; aryl esters; C–O activation; Pd-catalysis
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MDPI and ACS Style

Buchspies, J.; J. Pyle, D.; He, H.; Szostak, M. Pd-Catalyzed Suzuki-Miyaura Cross-Coupling of Pentafluorophenyl Esters. Molecules 2018, 23, 3134.

AMA Style

Buchspies J, J. Pyle D, He H, Szostak M. Pd-Catalyzed Suzuki-Miyaura Cross-Coupling of Pentafluorophenyl Esters. Molecules. 2018; 23(12):3134.

Chicago/Turabian Style

Buchspies, Jonathan, Daniel J. Pyle, Huixin He, and Michal Szostak. 2018. "Pd-Catalyzed Suzuki-Miyaura Cross-Coupling of Pentafluorophenyl Esters" Molecules 23, no. 12: 3134.

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