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Microwave Mediated Synthesis of an Arylboronate Library

Spencer, John and Baltus, Christine and Patel, Hiren and Press, Neil and Callear, Samantha K. and Male, Louise and Coles, Simon (2010) Microwave Mediated Synthesis of an Arylboronate Library. Journal of combinatorial chemistry, 13 (1). pp. 24-31. ISSN 1520-4766

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
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Keywords: Suzuki coupling; microwave; boronic acid; nucleophilic substitution; biaryls; supported reagents
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Date Deposited: 13 Oct 2015 13:16
Last Modified: 13 Oct 2015 13:16
URI: https://oak.novartis.com/id/eprint/3288

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