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. 2019 Jan 8;58(2):482-487.
doi: 10.1002/anie.201810947. Epub 2018 Dec 11.

Ruthenium-Catalyzed Reductive Arylation of N-(2-Pyridinyl)amides with Isopropanol and Arylboronate Esters

Thomas O Ronson  1 , Evelien Renders  1 , Ben F Van Steijvoort  1 , Xubin Wang  1 , Clarence C D Wybon  1 , Hana Prokopcová  2 , Lieven Meerpoel  2 , Bert U W Maes  1
Affiliations

Ruthenium-Catalyzed Reductive Arylation of N-(2-Pyridinyl)amides with Isopropanol and Arylboronate Esters

Thomas O Ronson et al. Angew Chem Int Ed Engl. .

Abstract

A new three-component reductive arylation of amides with stable reactants (iPrOH and arylboronate esters), making use of a 2-pyridinyl (Py) directing group, is described. The N-Py-amide substrates are readily prepared from carboxylic acids and PyNH2 , and the resulting N-Py-1-arylalkanamine reaction products are easily transformed into the corresponding chlorides by substitution of the HN-Py group with HCl. The 1-aryl-1-chloroalkane products allow substitution and cross-coupling reactions. Therefore, a general protocol for the transformation of carboxylic acids into a variety of functionalities is obtained. The Py-NH2 by-product can be recycled.

Keywords: amides; amines; arylation; multicomponent reactions; ruthenium.

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