Sterically-controlled intermolecular Friedel–Crafts acylation with twisted amides via selective N–C cleavage under mild conditions

Yongmei Liu; Guangrong Meng; Ruzhang Liu; Michal Szostak

doi:10.1039/C6CC02324J

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Sterically-controlled intermolecular Friedel–Crafts acylation with twisted amides via selective N–C cleavage under mild conditions†

Yongmei Liu,^ab Guangrong Meng,

^a Ruzhang Liu^b and Michal Szostak*^a

Author affiliations

* Corresponding authors

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

^b College of Chemistry and Chemical Engineering, Yangzhou University, 180 Siwangting Road, Yangzhou 225002, China
E-mail: michal.szostak@rutgers.edu

Abstract

Highly chemoselective Friedel–Crafts acylation with twisted amides under mild conditions is reported for the first time. The reaction shows high functional group tolerance, obviating the need for preformed sensitive organometallic reagents and expensive transition metal catalysts. The high reactivity of amides is switched on by ground-state steric distortion to disrupt the amide bond n_N → π_CO* resonance as a critical design feature. Conceptually, this new acid-promoted mechanism of twisted amides provides direct access to bench-stable acylating reagents under mild, metal-free conditions.

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Article information

DOI: https://doi.org/10.1039/C6CC02324J
Article type: Communication
Submitted: 17 Mar 2016
Accepted: 25 Apr 2016
First published: 03 May 2016

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Chem. Commun., 2016,52, 6841-6844

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Sterically-controlled intermolecular Friedel–Crafts acylation with twisted amides via selective N–C cleavage under mild conditions

Y. Liu, G. Meng, R. Liu and M. Szostak, Chem. Commun., 2016, 52, 6841 DOI: 10.1039/C6CC02324J

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Chemical Communications

Sterically-controlled intermolecular Friedel–Crafts acylation with twisted amides via selective N–C cleavage under mild conditions†

Abstract

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Sterically-controlled intermolecular Friedel–Crafts acylation with twisted amides via selective N–C cleavage under mild conditions

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