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

Ronson Thomas O. | Zendy; Renders Evelien | Zendy; Van Steijvoort Ben F. | Zendy; Wang Xubin | Zendy; Wybon Clarence C. D. | Zendy; Prokopcová Hana | Zendy; Meerpoel Lieven | Zendy; Maes Bert U. W. | Zendy

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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.

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