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Microwave-mediated synthesis of an arylboronate library

Microwave-mediated synthesis of an arylboronate library

Spencer, John, Baltus, Christine B., Patel, Hiren, Press, Neil J., Callear, Samantha K., Male, Louise and Coles, Simon J. (2010) Microwave-mediated synthesis of an arylboronate library. ACS Combinatorial Science, 2011 (13):1. pp. 24-31. ISSN 2156-8952 (Print), 2156-8944 (Online) (doi:10.1021/co100011g)

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Abstract

A series of arylboronates has been synthesized from the reaction of 2-(2-, (3-, or (4-(bromomethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 1{1−3} respectively with a range of N-, S-, and O-nucleophiles, using microwave-mediated chemistry. For the synthesis of N- and S-substituted boronates, a supported base, PS-NMM, was employed, and many reactions were complete within 15 min. With O-nucleophiles, a mixture of tetrabutylammonium bromide, potassium carbonate, and sodium hydroxide was employed. The resulting aminomethyl, mercaptomethyl, or alkoxy-/phenoxymethyl-arylboronates were subjected to microwave-mediated Suzuki Miyaura coupling reactions to afford a range of biaryls in moderate to good yields. The X-ray structures of five boronates were determined.

Item Type: Article
Uncontrolled Keywords: Suzuki coupling, microwave, boronic acid, nucleophilic substitution, biaryls, supported reagents
Subjects: Q Science > QD Chemistry
Pre-2014 Departments: School of Science
Related URLs:
Last Modified: 14 Oct 2016 09:15
Selected for GREAT 2016: None
Selected for GREAT 2017: None
Selected for GREAT 2018: None
URI: http://gala.gre.ac.uk/id/eprint/5843

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