Synthesis of functionalised fluorinated pyridine derivatives by site-selective Suzuki-Miyaura cross-coupling reactions of halogenated pyridines-Reference-Cited by-同舟云学术

Synthesis of functionalised fluorinated pyridine derivatives by site-selective Suzuki-Miyaura cross-coupling reactions of halogenated pyridines

Published:2017-03-28 Issue:4 Volume:72 Page:263-279
ISSN:1865-7117
Container-title:Zeitschrift für Naturforschung B
language:en
Short-container-title:

Author:

Sharif Muhammad¹²³,Shoaib Khurram¹⁴,Ahmed Shahzad¹⁴,Reimann Sebastian¹²,Iqbal Jamshed⁴,Hashmi Muhammad Ali⁵,Ayub Khurshid⁵,Yelibayeva Nazym⁶,Ospanov Meirambek⁶,Turmukhanova Mirgul Zh.⁶,Abilov Zharylkasyn A.⁶,Langer Peter¹²

Affiliation:

1. Institut für Chemie, Universität Rostock, Albert-Einstein-Str. 3a, 18059 Rostock, Germany

2. Leibniz-Institut für Katalyse an der Universität Rostock e. V., Albert-Einstein-Str. 29a, 18059 Rostock, Germany

3. College of Science, Chemistry Department, King Fahd University of Petroleum and Minerals, Dhahran 31261, Saudi Arabia

4. Department of Pharmacy, COMSATS Institute of Information Technology, Abbottabad 22060, Pakistan

5. Department of Chemistry, COMSATS Institute of Information Technology 22060, Abbottabad, Pakistan

6. Al-Farabi Kazakh National University, Al-Farabi ave. 71, 050040 Almaty, Kazakhstan

Abstract

Abstract The Suzuki-Miyaura reaction of 2,6-dichloro-3-(trifluoromethyl)pyridine with 1 equiv of arylboronic acids resulted in site-selective formation of 2-aryl-6-chloro-3-(trifluoromethyl)pyridine. Due to electronic reasons, the reaction takes place at the sterically more hindered position. The selectivity was rationalised by DFT calculations. The one-pot reaction with two different arylboronic acids afforded 2,6-diaryl-3-(trifluoromethyl)pyridine containing two different aryl substituents. The reactions proceeded smoothly in the absence of phosphine ligands. In addition, Suzuki-Miyaura reactions of 2,6-dichloro-4-(trifluoromethyl)pyridine with one or two equivalents of arylboronic acids were carried out.

Publisher

Walter de Gruyter GmbH

Subject

General Chemistry

Link

https://www.degruyter.com/document/doi/10.1515/znb-2016-0213/pdf

Reference52 articles.

1. F. Dorn, F. Montavon, M. Suchy, US4753947 A, 1988.

2. G. Hamprecht, N. Goetz, B. Wuerzer, K. O. Westphalen, EP0422456 B1, 1995.

3. B. Zehnder, Google Patents, 1987.

4. B. Zehnder, EP0209854 A2, 1987.

5. G. Li, X. Qian, J. Cui, Q. Huang, R. Zhang, H. Guan, J. Agric. Food Chem.2005, 54, 125.

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