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

被引：23

作者：

Ronson, Thomas O. ^{[1
]}

Renders, Evelien ^{[1
]}

Van Steijvoort, Ben F. ^{[1
]}

Wang, Xubin ^{[1
]}

Wybon, Clarence C. D. ^{[1
]}

Prokopcova, Hana ^{[2
]}

Meerpoel, Lieven ^{[2
]}

Maes, Bert U. W. ^{[1
]}

机构：

[1] Univ Antwerp, Dept Chem, Organ Synth, Groenenborgerlaan 171, B-2020 Antwerp, Belgium

[2] Janssen Pharmaceut NV, Janssen Res & Dev, Turnhoutseweg 30, B-2340 Beerse, Belgium

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2019年 / 58卷 / 02期

关键词：

amides; amines; arylation; multicomponent reactions; ruthenium; TERTIARY AMIDES; CHEMOSELECTIVE REDUCTION; NUCLEOPHILIC-ADDITION; TRIFLIC ANHYDRIDE; SECONDARY AMIDES; NICKEL; BOND; FUNCTIONALIZATION; AMINES; HYDROGENATION;

D O I：

10.1002/anie.201810947

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

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.

引用

页码：482 / 487

页数：6

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