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Ruthenium‐Catalyzed Reductive Arylation of N ‐(2‐Pyridinyl)amides with Isopropanol and Arylboronate Esters
Author(s) -
Ronson Thomas O.,
Renders Evelien,
Van Steijvoort Ben F.,
Wang Xubin,
Wybon Clarence C. D.,
Prokopcová Hana,
Meerpoel Lieven,
Maes Bert U. W.
Publication year - 2019
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201810947
Subject(s) - chemistry , amide , catalysis , aryl , ruthenium , medicinal chemistry , group (periodic table) , organic chemistry , combinatorial chemistry , alkyl
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 PyNH 2 , 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‐NH 2 by‐product can be recycled.