Spencer, John, Baltus, Christine, Patel, Hiren, Press, Neil, Callear, Samantha K., 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
Related URLs:	http://pubs.acs.org/loi/jcchff http://www.ncbi.nlm.nih.gov/sites/entrez
Additional Information:	archiving not formally supported by this publisher
Keywords:	Suzuki coupling; microwave; boronic acid; nucleophilic substitution; biaryls; supported reagents
Related URLs:	http://pubs.acs.org/loi/jcchff http://www.ncbi.nlm.nih.gov/sites/entrez
Date Deposited:	13 Oct 2015 13:16
Last Modified:	13 Oct 2015 13:16
URI:	https://oak.novartis.com/id/eprint/3288