Directed Remote Aromatic Metalations: Mechanisms and Driving Forces

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Tilly, David
Magolan, Jakob
Mortier, Jacques
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2012
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Abstract

Directed remote aromatic metalations are useful synthetic transformations allowing for rapid regioselective access to elaborate highly substituted carbocyclic aromatic and heteroaromatic systems. This review unravels the tangle of data reported on directed remote aromatic metalations. Through a careful analysis of critically selected examples, advanced rationalizations of remote metalation regioselectivities are presented. These extend beyond the complex-induced proximity effect (CIPE). Mechanisms, driving forces, and parameters influencing remote metalations are discussed. An understanding of these metalation mechanisms enables more accurate predictability of justification of regiochemical outcomes of these useful synthetic transformations.

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Chemistry - A European Journal

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18

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13

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© 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. This is the pre-peer reviewed version of the following article: Directed Remote Aromatic Metalations: Mechanisms and Driving Forces, Chemistry - A European Journal, Vol. 18(13), 2012, pp. 3804-3820, which has been published in final form at http://Dx.doi.org/10.1002/chem.201103920.

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Chemical Sciences not elsewhere classified

Chemical Sciences

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